752:(DPPF) as ligands for the Buchwald–Hartwig amination provided the first reliable extension to primary amines and allowed efficient coupling of aryl iodides and triflates. (It is believed that the bidentate ligands prevent formation of the palladium iodide dimer after oxidative addition, speeding up the reaction.) These ligands typically produce the coupled products at higher rates and better yields than the first generation of catalysts. The initial reports of these ligands as catalysts were somewhat unexpected given the mechanistic evidence for monoligated complexes serving as the active catalysts in the first-generation system. In fact, the first examples from both labs were published in the same issue of
655:(Chelating systems have been shown to undergo these two steps in reverse order, with base complexation preceding amide formation.) This key intermediate reductively eliminates to produce the product and regenerate the catalyst. However, a side reaction can occur wherein β-hydride elimination followed by reductive elimination produces the hydrodehalogenated arene and the corresponding imine. Not shown are additional equilibria wherein various intermediates coordinate to additional phosphine ligands at various stages in the catalytic cycle.
496:
369:
733:
628:
891:
801:
766:
857:
1026:
938:
473:
36:
274:
324:
535:
988:
411:
716:) catalyst system was found to be effective for the coupling of both cyclic and acyclic secondary amines bearing both alkyl and aryl functionality (though not diarylamines) with a variety of aryl bromides. In general, these conditions were not able to couple primary amines due to competitive hydrodehalogenation of the arene.
879:
The dramatic increase in activity seen with these ligands is attributed to their propensity to sterically favor the monoligated palladium species at all stages of the catalytic cycle, dramatically increasing the rate of oxidative addition, amide formation, and reductive elimination. Several of these
687:
Although the scope of the
Buchwald–Hartwig amination has been expanded to include a wide variety of aryl and amine coupling partners, the conditions required for any particular reactants are still largely substrate dependent. Various ligand systems have been developed, each with varying capabilities
1017:
Enolates and other similar carbon nucleophiles can also be coupled to produce α-aryl ketones, malonates, nitriles, etc. The scope of this transformation is similarly ligand-dependent and a number of systems have been developed. Several enantioselective methods for this process have been developed.
280:
Over the course of its development, several 'generations' of catalyst systems have been developed, with each system allowing greater scope in terms of coupling partners and milder conditions, allowing virtually any amine to be coupled with a wide variety of aryl coupling partners. Because of the
654:
with the μ-halogen dimer. The stability of this dimer decreases in the order of X = I > Br > Cl, and is thought to be responsible for the slow reaction of aryl iodides with the first-generation catalyst system. Amine ligation followed by deprotonation by base produces the palladium amide.
828:
Bulky tri- and di-alkyl phosphine ligands have been shown to be remarkably active catalysts, allowing the coupling of a wide range of amines (primary, secondary, electron withdrawn, heterocyclic, etc.) with aryl chlorides, bromides, iodides, and triflates. Additionally, reactions employing
592:
for this reaction has been demonstrated to proceed through steps similar to those known for palladium catalyzed CC coupling reactions. Steps include oxidative addition of the aryl halide to a Pd(0) species, addition of the amine to the oxidative addition complex, deprotonation followed by
662:
Pd complexes. The
Hartwig group found that "reductive elimination can occur from either a four-coordinate bisphosphine or three-coordinate monophosphine arylpalladium amido complex. Eliminations from the three-coordinate compounds are faster. Second, β-hydrogen elimination occurs from a
921:
remains one of the most challenging coupling partners for
Buchwald–Hartwig amination reactions, a problem attributed to its tight binding with palladium complexes. Several strategies have been developed to overcome this based on reagents that serve as ammonia equivalents. The use of a
1376:
Hartwig, J.F.; Richards, S.; Barañano, D.; Paul, F. (1996), "Influences on the
Relative Rates for C−N Bond-Forming Reductive Elimination and β-Hydrogen Elimination of Amides. A Case Study on the Origins of Competing Reduction in the Palladium-Catalyzed Amination of Aryl Halides",
792:
from these ligands is thought to suppress β-hydride elimination by preventing an open coordination site. In fact, α-chiral amines were found not to racemize when chelating ligands were employed, in contrast to the first-generation catalyst system.
688:
and limitations, and the choice of conditions requires consideration of the steric and electronic properties of both partners. Detailed below are the substrates and conditions for the major generations of ligand systems. (Not included herein are
2085:
Huang, X.; Anderson, K.W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S.L. (2003), "Expanding Pd-Catalyzed C–N Bond-Forming
Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions",
1981:
Hamann, B.C.; Hartwig, J.F. (1998), "Sterically
Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and Chlorides, and the First Amination of Aryl Tosylates",
2120:
Anderson, K.W.; Tundel, R.E.; Ikawa, T.; Altman, R.A.; Buchwald, S.L. (2006), "Monodentate
Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C–N Bond-Forming Reactions of Heteroaromatic Halides/Amines and (H)N-Heterocycles",
663:
three-coordinate intermediate. Therefore, β-hydrogen elimination occurs slowly from arylpalladium complexes containing chelating phosphines while reductive elimination can still occur from these four-coordinate species."
2328:
Mann, G.; Incarvito, C.; Rheingold, A.L.; Hartwig, J.F. (1999), "Palladium-Catalyzed C–O Coupling
Involving Unactivated Aryl Halides. Sterically Induced Reductive Elimination To Form the C–O Bond in Diaryl Ethers",
604:
Throughout the development of the reaction the group sought to identify reaction intermediates through fundamental mechanistic studies. These studies have revealed a divergent reaction pathways depending on whether
1186:
Paul,F.; Patt, J.; Hartwig, J.F. (1994), "Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides",
461:. Secondly, the yield for electron rich and electron poor arenes was improved via minor modifications to the reaction procedure (higher catalyst loading, higher temperature, longer reaction time), although no
1835:
Wolfe, J.P.; Wagaw, S.; Buchwald, S.L. (1996), "An
Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates",
237:
have been credited, whose publications between 1994 and the late 2000s established the scope of the transformation. The reaction's synthetic utility stems primarily from the shortcomings of typical methods
2155:
Ikawa, T.; Barder, T.E.; Biscoe, M.R.; Buchwald, S.L. (2007), "Pd-Catalyzed
Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation",
1920:
Old, D.W.; Wolfe, J.P.; Buchwald, S.L. (1998), "A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides",
297:
The first example of a palladium catalyzed C–N cross-coupling reaction was published in 1983 by Migita and coworkers and described a reaction between several aryl bromides and N,N-diethylamino-tributyl
5727:
2049:
Stambuli, J.P.; Kuwano, R.; Hartwig, J.F. (2002), "Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room Temperature",
1429:
Widenhoefer, R.A.; Buchwald, S.L. (1996), "Halide and Amine Influence in the Equilibrium Formation of Palladium Tris(o-tolyl)phosphine Mono(amine) Complexes from Palladium Aryl Halide Dimers",
1010:
Thiols and thiophenols can be coupled with aryl halides under Buchwald-Hartwig-type conditions to produce the corresponding aryl thioethers. Furthermore, mercaptoesters have been employed as H
391:
These reports were virtually uncited for a decade. In February 1994, Hartwig reported a systematic study of the palladium compounds involved in the original Migita paper, concluding that the
2284:
Vo, G.D.; Hartwig, J.F. (2009), "Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines",
679:
and the industrial preparation of numerous pharmaceuticals. Industrial applications include α-arylation of carbonyl compounds (such as ketones, esters, amides, aldehydes) and nitriles.
1809:
Driver, M.S.; Hartwig, J.F. (1996), "A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl2",
1403:
Driver, M.S.; Hartwig, J.F. (1995), "A Rare, Low-Valent Alkylamido Complex, a Diphenylamido Complex, and Their Reductive Elimination of Amines by Three-Coordinate Intermediates",
2547:
2216:
Lee, S.; Jorgensen, M.; Hartwig, J.F. (2001), "Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent",
4843:
4788:
2190:
Wolfe, J.P.; Ahman, J.; Sadighi, J.P.; Singer, R.A.; Buchwald, S.L. (1997), "An Ammonia Equivalent for the Palladium-Catalyzed Amination of Aryl Halides and Triflates",
597:. An unproductive side reaction can compete with reductive elimination wherein the amide undergoes beta hydride elimination to yield the hydrodehalogenated arene and an
5556:
350:
and James S. Panek reported an example of Pd(0)-mediated C–N bond formation in the context of their work on the synthesis of lavendamycin which utilized stoichiometric
4898:
1246:
Louie,J.; Hartwig, J.F. (1995), "Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents",
2539:
2484:
Liao, X.; Weng, Z.; Hartwig, J.F. (2008), "Enantioselective r-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel",
519:-free coupling. Though these improved conditions proceeded at a faster rate, the substrate scope was limited almost entirely to secondary amines due to competitive
5048:
3682:
2389:
Heesgaard Jepsen Tue (2011). "Synthesis of Functionalized Dibenzothiophenes - An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and CS Bond Formations".
5777:
5551:
883:
Even electron withdrawn amines and heterocyclic substrates can be coupled under these conditions, despite their tendency to deactivate the palladium catalyst.
4653:
1072:
Forero-Cortés, Paola A.; Haydl, Alexander M. (2 July 2019). "The 25th Anniversary of the Buchwald–Hartwig Amination: Development, Applications, and Outlook".
3377:
4423:
2574:
557:
These results established the so-called "first generation" of Buchwald–Hartwig catalyst systems. The following years saw development of more sophisticated
5223:
3167:
5318:
3422:
1864:
Louie, J.; Driver, M.S.; Hamann, B.C.; Hartwig, J.F. (1997), "Palladium-Catalyzed Amination of Aryl Triflates and Importance of Triflate Addition Rate",
1554:
Wolfe, J.P.; Wagaw, S.; Marcoux, J.F.; Buchwald, S.L. (1998), "Rational Development of Practical Catalysts for Aromatic Carbon-Nitrogen Bond Formation",
256:
tolerance. The development of the Buchwald–Hartwig reaction allowed for the facile synthesis of aryl amines, replacing to an extent harsher methods (the
5298:
4793:
3960:
880:
ligands also seem to enhance the rate of reductive elimination relative to β-hydride elimination via the electron donating arene-palladium interaction.
368:
3841:
3397:
890:
5388:
754:
658:
For chelating ligands, the monophosphine palladium species is not formed; oxidative addition, amide formation and reductive elimination occur from L
5143:
1025:
2610:
1283:
576:
eventually became suitable substrates, and reactions run with weaker bases at room temperature were developed. These advances are detailed in the
3975:
1583:
Hartwig, J.F. (1998), "Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism",
749:
627:
100:
5621:
5078:
5571:
1350:
Driver, M.S.; Hartwig, J.F. (1997), "Carbon−Nitrogen-Bond-Forming Reductive Elimination of Arylamines from Palladium(II) Phosphine Complexes",
72:
5183:
5163:
5123:
3930:
5717:
5642:
5526:
4138:
3542:
2873:
1960:
1596:
1335:
351:
5712:
5541:
5198:
5053:
4683:
2355:
Torraca, K.E.; Huang, X.; Parrish, C.A.; Buchwald, S.L. (2001), "An Efficient Intermolecular Palladium-Catalyzed Synthesis of Aryl Ethers",
188:
4528:
3765:
1132:
Kosugi, M.; Kameyama, M.; Migita, T. (1983), "Palladium-Catalyzed Aromatic Amination of Aryl Bromides With n,n-Di-Ethylamino-Tributyltin",
4888:
4378:
4053:
800:
79:
5792:
5576:
4598:
1947:
Wolfe, J.P.; Buchwald, S.L. (1999), "A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides",
1764:
5153:
856:
5787:
5501:
5363:
5118:
841:
bases in place of the traditional alkoxide and silylamide bases have been developed. The Buchwald group has developed a wide range of
261:
5677:
5148:
5063:
5033:
5013:
4878:
4873:
4248:
4173:
3816:
3770:
3637:
2898:
937:
503:
In 1995, back to back studies from each lab showed that the couplings could be conducted with free amines in the presence of a bulky
5616:
1158:
Boger, D.L.; Panek, J.S. (1984), "Palladium(0)- mediated -carboline synthesis: Preparation of the CDE ring system of lavendamycin",
119:
86:
5782:
5742:
5692:
5168:
4918:
4848:
3337:
2450:
Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S.L. (2002), "An Improved Catalyst for the Asymmetric Arylation of Ketone Enolates",
5378:
4983:
3876:
3597:
1281:
Guram, A.S.; Rennels, R.A.; Buchwald, S.L. (1995), "A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines",
650:
For monodentate ligand systems the monophosphine palladium (0) species is believed to form the palladium (II) species which is in
5368:
2908:
613:
phosphine ligands are employed in the reaction, and a number of nuanced influences have been revealed (especially concerning the
433:
In May 1994, Buchwald published an extension of the Migita paper offering two major improvements over the original paper. First,
5536:
5293:
5243:
4033:
3965:
3856:
3432:
3187:
3112:
2893:
5876:
5248:
5058:
4533:
4443:
2567:
1892:
Wagaw, S.; Rennels, R.A.; Buchwald, S.L. (1997), "Palladium-Catalyzed Coupling of Optically Active Amines with Aryl Bromides",
842:
614:
68:
5822:
5606:
5546:
4948:
4923:
4833:
4413:
4293:
3327:
2823:
5707:
5193:
4988:
3257:
1116:
57:
50:
5812:
5398:
4908:
4418:
4363:
4208:
4168:
4000:
3755:
3472:
3322:
1620:
Hartwig, J.F. (2008), "Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides",
323:
5772:
5333:
5288:
4778:
4633:
5807:
5722:
5581:
5496:
5393:
4468:
4123:
3791:
3202:
2763:
5697:
5672:
5657:
5353:
5218:
5173:
4938:
4483:
4333:
3547:
3227:
3172:
5702:
5647:
5178:
4593:
4308:
4303:
3796:
3612:
3602:
3317:
3177:
3127:
3122:
3097:
3003:
5871:
5757:
5358:
5278:
4893:
4858:
4703:
4128:
4088:
3985:
3760:
3512:
3457:
3057:
2768:
2758:
2733:
765:
462:
5732:
5433:
5238:
4673:
4238:
4213:
4153:
3745:
3452:
3102:
1215:
Guram, A.S.; Buchwald, S.L. (1994), "Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes",
3287:
2010:"Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates"
5023:
4558:
4010:
3232:
3197:
2793:
2728:
2560:
309:
181:
5591:
5213:
4273:
4198:
3722:
3557:
3242:
3018:
2978:
2723:
2545:
Buchwald–Hartwig reaction Precious-Metal catalysts from Acros Organics for coupling reactions in organic synthesis
2530:
1458:
Hartwig, J.F. (1999), "Approaches to catalyst discovery. New carbon-heteroatom and carbon-carbon bond formation",
173:
5832:
5737:
5471:
5443:
5413:
5328:
5258:
5188:
5108:
5008:
4968:
4663:
4283:
3582:
3577:
3039:
2903:
239:
5797:
5667:
5531:
5373:
5233:
4753:
3727:
3277:
3237:
2988:
214:
93:
5687:
5283:
5253:
5128:
5083:
4913:
4823:
4638:
4628:
4458:
4015:
3955:
3920:
3707:
3667:
3442:
3312:
2828:
2818:
2748:
1528:
Hartwig, J.F. (1998), "Carbon-Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides",
1494:
Hartwig, J.F. (1997), "Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst Design",
520:
5263:
4243:
3267:
2813:
2693:
495:
5476:
534:
5881:
5767:
5626:
5418:
5343:
5323:
5043:
4993:
4853:
4818:
4758:
4688:
3990:
3970:
3702:
3622:
3517:
3477:
3447:
3382:
3252:
3162:
3152:
3028:
2738:
2250:
Huang, X.; Buchwald, S.L. (2001), "New Ammonia Equivalents for the Pd-Catalyzed Amination of Aryl Halides",
720:
472:
218:
46:
5506:
5228:
4978:
4958:
4933:
4883:
4798:
4773:
4728:
4698:
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4613:
4568:
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4328:
4108:
3801:
3737:
3537:
3262:
3182:
2868:
2843:
2620:
2615:
2416:
Culkin, D.A.; Hartwig, J.F. (2003), "Palladium-Catalyzed r-Arylation of Carbonyl Compounds and Nitriles",
1711:
Surry, D.S.; Buchwald, S.L. (2011), "Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide",
689:
5842:
4588:
3212:
5428:
5383:
5098:
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5038:
4973:
4953:
4868:
4863:
4828:
4783:
4768:
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4733:
4668:
4658:
4538:
4058:
3861:
3437:
3392:
3222:
2958:
2678:
2640:
594:
2888:
2883:
5481:
5611:
5561:
5511:
5491:
5338:
5313:
5028:
5018:
4903:
4718:
4713:
4643:
4428:
4228:
4188:
4118:
4083:
4038:
4005:
3871:
3846:
3826:
3647:
3607:
3567:
3532:
3462:
3217:
3087:
3062:
2600:
977:
651:
508:
248:
5827:
5817:
5802:
5448:
5423:
5408:
5403:
5133:
5088:
5073:
4963:
4943:
4838:
4723:
4708:
4553:
4498:
4488:
4478:
4453:
4218:
4093:
4068:
3980:
3836:
3821:
3806:
3662:
3627:
3572:
3342:
3192:
3137:
3008:
2923:
2783:
2708:
1314:
Muci, A.R.; Buchwald, S.L. (2002), "Practical Palladium Catalysts for C–N and C–O Bond Formation",
1248:
1160:
969:
243:
230:
143:
2853:
5566:
5516:
5486:
5348:
5138:
4928:
4813:
4748:
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4398:
4393:
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4313:
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3831:
3617:
3562:
3492:
3412:
3307:
3207:
3142:
3067:
2913:
2778:
2713:
1667:
Surry, D.S.; Buchwald, S.L. (2008), "Biaryl Phosphane Ligands in Palladium-Catalyzed Amination",
1511:
1477:
1089:
987:
923:
589:
400:
2698:
732:
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4508:
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4133:
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3082:
3077:
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2838:
2798:
2753:
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2630:
2595:
2511:
2467:
2433:
2372:
2311:
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2233:
2173:
2138:
2103:
2068:
2032:
2009:
1964:
1894:
1838:
1738:
1694:
1647:
1600:
1331:
1217:
1189:
1112:
926:
or silylamide can overcome this limitation, with subsequent hydrolysis furnishing the primary
257:
210:
202:
157:
1761:
580:
section below, and the extension to more complex systems remains an active area of research.
5837:
5682:
5652:
5596:
5521:
5453:
5208:
5158:
5003:
4808:
4583:
4578:
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2501:
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2425:
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2301:
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2259:
2225:
2199:
2165:
2130:
2095:
2058:
2024:
1991:
1956:
1930:
1903:
1875:
1847:
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1728:
1720:
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1629:
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1438:
1412:
1386:
1359:
1323:
1292:
1257:
1226:
1198:
1169:
1141:
1081:
976:. This serves as a convenient replacement for harsher analogues of this process such as the
675:, the reaction has gained wide use in synthetic organic chemistry, with application in many
504:
313:
285:, the reaction has gained wide use in synthetic organic chemistry, with application in many
253:
5747:
5438:
5273:
5268:
4563:
4548:
4493:
4448:
4408:
4358:
4323:
4318:
4263:
4258:
4193:
4143:
4063:
3891:
3775:
3750:
3712:
3687:
3672:
3657:
3592:
3467:
3417:
3407:
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3157:
3147:
3132:
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1768:
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672:
454:
286:
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234:
147:
17:
2718:
2688:
410:
5752:
5662:
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4348:
4203:
3940:
3717:
3587:
3402:
3372:
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2968:
2743:
2605:
2506:
2306:
1781:
Wolfe, J. P.; Buchwald, S. L. (1996), "Palladium-Catalyzed Amination of Aryl Iodides",
1733:
1689:
1642:
789:
724:
610:
434:
2203:
1173:
1014:
S-equivalents in order to generate the thiophenol from the corresponding aryl halide.
727:
only if dioxane was used in place of toluene as a solvent, albeit with modest yields.
5865:
5762:
5463:
5308:
5203:
4998:
4388:
4353:
4343:
4278:
4268:
4158:
3995:
3811:
3522:
3497:
3367:
3013:
2998:
2983:
2878:
2808:
2788:
2703:
1866:
1783:
1515:
1262:
1093:
347:
1481:
4803:
4163:
3915:
3692:
3292:
3092:
2943:
2938:
2803:
2658:
450:
960:
A catalyst system that can directly couple ammonia using a Josiphos-type ligand.
3302:
2948:
2918:
2683:
1961:
10.1002/(sici)1521-3773(19990816)38:16<2413::aid-anie2413>3.0.co;2-h
1597:
10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l
606:
226:
35:
5586:
5113:
4463:
2552:
693:
273:
1085:
1472:
1327:
846:
838:
834:
830:
558:
516:
392:
2515:
2471:
2437:
2402:
2376:
2315:
2271:
2237:
2177:
2142:
2134:
2107:
2072:
2063:
2036:
1968:
1742:
1698:
1680:
1651:
1604:
1296:
564:
that allowed extension to a larger variety of amines and aryl groups. Aryl
2993:
2663:
701:
697:
573:
569:
2463:
2008:
Wolfe, J.P.; Tomori, H.; Sadighi, J.P.; Yin, J.; Buchwald, S.L. (2000),
1934:
1416:
1230:
1202:
1145:
2653:
1724:
1507:
927:
918:
561:
458:
2497:
2429:
2368:
2342:
2297:
2263:
2229:
2169:
2099:
2028:
1995:
1907:
1879:
1851:
1822:
1796:
1762:
The 2010 Nobel Prize in Chemistry: Palladium-Catalysed Cross-Coupling.
1633:
1567:
1541:
1442:
1390:
1363:
229:. Although Pd-catalyzed C–N couplings were reported as early as 1983,
1053:
1049:
565:
512:
252:
bonds, with most methods suffering from limited substrate scope and
1111:(4th ed.). New York: John Wiley & Sons, Inc. p. 461.
972:
can be coupled with aryl halides to produce the corresponding aryl
399:
was the active catalyst. Proposed was a catalytic cycle involving
1029:
Enolate coupling as an extension of the Buchwald–Hartwig amination
973:
745:
598:
494:
446:
222:
671:
Because of the ubiquity of aryl C–N bonds in pharmaceuticals and
264:, etc.) while significantly expanding the repertoire of possible
1771:
Platinum Metals Rev., 2011, 55, (2) doi:10.1595/147106711X558301
894:
Heteoaryl and amide substrates in the Buchwald–Hartwig amination
3037:
2556:
361:. Attempts to render the reaction catalytic were unsuccessful.
298:
29:
465:-substituted aryl groups were included in this publication.
1024:
986:
936:
889:
855:
799:
764:
723:
variant of this reaction, and importantly, could be coupled
626:
533:
471:
409:
372:
C–N coupling reaction in the total synthesis of lavendamycin
367:
322:
289:
and the industrial preparation of numerous pharmaceuticals.
1107:
Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.).
968:
Under conditions similar to those employed for amination,
719:
Aryl iodides were found to be suitable substrates for the
1048:
Several versions of the reaction employing complexes of
964:
Variations on C–N couplings: C–O, C–S, and C–C couplings
631:
Catalytic cycle for monodentate phosphine ligand systems
1662:
1660:
941:
Ammonia equivalents in the Buchwald–Hartwig amination
453:
allowed extension of the methodology to a variety of
5728:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
1578:
1576:
1453:
1451:
1309:
1307:
1305:
5635:
5462:
5097:
4612:
4107:
4024:
3904:
3784:
3736:
3046:
2538:Ian Mangion MacMillan Group Meeting July 30, 2002
281:ubiquity of aryl C–N bonds in pharmaceuticals and
4789:Divinylcyclopropane-cycloheptadiene rearrangement
308:. Though several aryl bromides were tested, only
1056:rather than palladium have also been developed.
327:Original precedent for Pd-catalyzed C–N coupling
860:Bulky ligands in the Buchwald–Hartwig amination
804:Chiral retention by chelating phosphine ligands
5049:Thermal rearrangement of aromatic hydrocarbons
3683:Thermal rearrangement of aromatic hydrocarbons
1615:
1613:
1109:Weygand/Hilgetag Preparative Organic Chemistry
704:which also have been developed considerably.)
5778:Lectka enantioselective beta-lactam synthesis
2568:
2531:Buchwald–Hartwig Coupling – Recent Literature
8:
5557:Inverse electron-demand Diels–Alder reaction
3378:Heterogeneous metal catalyzed cross-coupling
27:Chemical reaction for synthesizing C–N bonds
4899:Lobry de Bruyn–Van Ekenstein transformation
1276:
1274:
1272:
5459:
3733:
3034:
2575:
2561:
2553:
1241:
1239:
1074:Organic Process Research & Development
515:in the Hartwig publication), allowing for
316:substrates gave good to excellent yields.
131:
5389:Petrenko-Kritschenko piperidone synthesis
4844:Fritsch–Buttenberg–Wiechell rearrangement
2505:
2305:
2062:
1732:
1688:
1641:
1471:
1261:
849:-derived and trialkyl phosphine ligands.
845:, while the Hartwig group has focused on
620:The catalytic cycle proceeds as follows:
120:Learn how and when to remove this message
5552:Intramolecular Diels–Alder cycloaddition
1284:Angewandte Chemie International Edition
1064:
499:Stephen L. Buchwald and John F. Hartwig
5572:Metal-centered cycloaddition reactions
5224:Debus–Radziszewski imidazole synthesis
3168:Bodroux–Chichibabin aldehyde synthesis
457:(both cyclic and acyclic) and primary
246:, etc.) for the synthesis of aromatic
219:palladium-catalyzed coupling reactions
56:Please improve this article by adding
5718:Diazoalkane 1,3-dipolar cycloaddition
5622:Vinylcyclopropane (5+2) cycloaddition
5527:Diazoalkane 1,3-dipolar cycloaddition
5299:Hurd–Mori 1,2,3-thiadiazole synthesis
4794:Dowd–Beckwith ring-expansion reaction
3961:Hurd–Mori 1,2,3-thiadiazole synthesis
2874:LFER solvent coefficients (data page)
2391:European Journal of Organic Chemistry
7:
4529:Sharpless asymmetric dihydroxylation
3766:Methoxymethylenetriphenylphosphorane
1020:
982:
932:
885:
851:
795:
760:
622:
529:
467:
405:
363:
318:
4654:Allen–Millar–Trippett rearrangement
5793:Nitrone-olefin (3+2) cycloaddition
5788:Niementowski quinazoline synthesis
5577:Nitrone-olefin (3+2) cycloaddition
5502:Azide-alkyne Huisgen cycloaddition
5364:Niementowski quinazoline synthesis
5119:Azide-alkyne Huisgen cycloaddition
4424:Meerwein–Ponndorf–Verley reduction
3976:Leimgruber–Batcho indole synthesis
262:nucleophilic aromatic substitution
25:
5617:Trimethylenemethane cycloaddition
5319:Johnson–Corey–Chaykovsky reaction
5184:Cadogan–Sundberg indole synthesis
5164:Bohlmann–Rahtz pyridine synthesis
5124:Baeyer–Emmerling indole synthesis
3931:Cadogan–Sundberg indole synthesis
3423:Johnson–Corey–Chaykovsky reaction
538:1995 Tin-free coupling conditions
5713:Cook–Heilbron thiazole synthesis
5542:Hexadehydro Diels–Alder reaction
5369:Niementowski quinoline synthesis
5199:Cook–Heilbron thiazole synthesis
5144:Bischler–Möhlau indole synthesis
5054:Tiffeneau–Demjanov rearrangement
4684:Baker–Venkataraman rearrangement
3842:Horner–Wadsworth–Emmons reaction
3513:Mizoroki-Heck vs. Reductive Heck
3398:Horner–Wadsworth–Emmons reaction
2909:Neighbouring group participation
731:
708:First-generation catalyst system
272:
34:
5249:Fiesselmann thiophene synthesis
5079:Westphalen–Lettré rearrangement
5059:Vinylcyclopropane rearrangement
4889:Kornblum–DeLaMare rearrangement
4534:Epoxidation of allylic alcohols
4444:Noyori asymmetric hydrogenation
4379:Kornblum–DeLaMare rearrangement
4054:Gallagher–Hollander degradation
1318:, Topics in Current Chemistry,
843:dialkylbiaryl phosphine ligands
615:dialkylbiaryl phosphine ligands
5708:Chichibabin pyridine synthesis
5194:Chichibabin pyridine synthesis
5154:Blum–Ittah aziridine synthesis
4989:Ring expansion and contraction
3258:Cross dehydrogenative coupling
692:ligands and ligands with wide
524:
1:
5678:Bischler–Napieralski reaction
5636:Heterocycle forming reactions
5289:Hemetsberger indole synthesis
5149:Bischler–Napieralski reaction
5064:Wagner–Meerwein rearrangement
5034:Sommelet–Hauser rearrangement
5014:Seyferth–Gilbert homologation
4879:Ireland–Claisen rearrangement
4874:Hofmann–Martius rearrangement
4634:2,3-sigmatropic rearrangement
4249:Corey–Winter olefin synthesis
4174:Barton–McCombie deoxygenation
3817:Corey–Winter olefin synthesis
3771:Seyferth–Gilbert homologation
3638:Seyferth–Gilbert homologation
2204:10.1016/S0040-4039(97)01465-2
1174:10.1016/S0040-4039(01)91001-9
511:in the Buchwald publication,
449:purge to remove the volatile
58:secondary or tertiary sources
5783:Lehmstedt–Tanasescu reaction
5743:Gabriel–Colman rearrangement
5698:Bucherer carbazole synthesis
5693:Borsche–Drechsel cyclization
5673:Bernthsen acridine synthesis
5658:Bamberger triazine synthesis
5643:Algar–Flynn–Oyamada reaction
5354:Nazarov cyclization reaction
5219:De Kimpe aziridine synthesis
5174:Bucherer carbazole synthesis
5169:Borsche–Drechsel cyclization
4939:Nazarov cyclization reaction
4919:Meyer–Schuster rearrangement
4849:Gabriel–Colman rearrangement
4599:Wolffenstein–Böters reaction
4484:Reduction of nitro compounds
4334:Grundmann aldehyde synthesis
4139:Algar–Flynn–Oyamada reaction
3548:Olefin conversion technology
3543:Nozaki–Hiyama–Kishi reaction
3338:Gabriel–Colman rearrangement
3228:Claisen-Schmidt condensation
3173:Bouveault aldehyde synthesis
1263:10.1016/0040-4039(95)00605-C
69:"Buchwald–Hartwig amination"
5758:Hantzsch pyridine synthesis
5537:Enone–alkene cycloadditions
5359:Nenitzescu indole synthesis
5279:Hantzsch pyridine synthesis
5244:Ferrario–Ackermann reaction
4894:Kowalski ester homologation
4859:Halogen dance rearrangement
4704:Benzilic acid rearrangement
4129:Akabori amino-acid reaction
4089:Von Braun amide degradation
4034:Barbier–Wieland degradation
3986:Nenitzescu indole synthesis
3966:Kharasch–Sosnovsky reaction
3857:Julia–Kocienski olefination
3761:Kowalski ester homologation
3458:Kowalski ester homologation
3433:Julia–Kocienski olefination
3188:Cadiot–Chodkiewicz coupling
3113:Aza-Baylis–Hillman reaction
3058:Acetoacetic ester synthesis
2769:Dynamic binding (chemistry)
2759:Conrotatory and disrotatory
2734:Charge remote fragmentation
824:Sterically hindered ligands
740:Bidentate phosphine ligands
135:Buchwald-Hartwig amination
5898:
5823:Robinson–Gabriel synthesis
5773:Kröhnke pyridine synthesis
5607:Retro-Diels–Alder reaction
5547:Imine Diels–Alder reaction
5334:Kröhnke pyridine synthesis
4949:Newman–Kwart rearrangement
4924:Mislow–Evans rearrangement
4834:Fischer–Hepp rearrangement
4779:Di-π-methane rearrangement
4559:Stephen aldehyde synthesis
4294:Eschweiler–Clarke reaction
4011:Williamson ether synthesis
3328:Fujiwara–Moritani reaction
3233:Combes quinoline synthesis
3198:Carbonyl olefin metathesis
2899:More O'Ferrall–Jencks plot
2824:Grunwald–Winstein equation
2794:Electron-withdrawing group
2729:Catalytic resonance theory
2536:Buchwald–Hartwig Chemistry
750:diphenylphosphinoferrocene
746:diphenylphosphinobinapthyl
577:
207:Buchwald–Hartwig amination
18:Buchwald-Hartwig amination
5833:Urech hydantoin synthesis
5813:Pomeranz–Fritsch reaction
5738:Fischer oxazole synthesis
5472:1,3-Dipolar cycloaddition
5444:Urech hydantoin synthesis
5414:Reissert indole synthesis
5399:Pomeranz–Fritsch reaction
5329:Knorr quinoline synthesis
5259:Fischer oxazole synthesis
5189:Camps quinoline synthesis
5109:1,3-Dipolar cycloaddition
5009:Semipinacol rearrangement
4984:Ramberg–Bäcklund reaction
4969:Piancatelli rearrangement
4909:McFadyen–Stevens reaction
4664:Alpha-ketol rearrangement
4419:McFadyen–Stevens reaction
4364:Kiliani–Fischer synthesis
4284:Elbs persulfate oxidation
4209:Bouveault–Blanc reduction
4169:Baeyer–Villiger oxidation
4001:Schotten–Baumann reaction
3877:Ramberg–Bäcklund reaction
3756:Kiliani–Fischer synthesis
3598:Ramberg–Bäcklund reaction
3583:Pinacol coupling reaction
3578:Piancatelli rearrangement
3473:Liebeskind–Srogl coupling
3323:Fujimoto–Belleau reaction
3040:List of organic reactions
2904:Negative hyperconjugation
2649:
2591:
769:Bidentate ligand examples
523:of the bromoarenes. (See
476:Buchwald 1994 publication
240:nucleophilic substitution
195:
174:buchwald-hartwig-reaction
169:Organic Chemistry Portal
163:
134:
5808:Pictet–Spengler reaction
5723:Einhorn–Brunner reaction
5688:Boger pyridine synthesis
5582:Oxo-Diels–Alder reaction
5497:Aza-Diels–Alder reaction
5394:Pictet–Spengler reaction
5294:Hofmann–Löffler reaction
5284:Hegedus indole synthesis
5254:Fischer indole synthesis
5129:Bartoli indole synthesis
5084:Willgerodt rearrangement
4914:McLafferty rearrangement
4824:Ferrier carbocyclization
4639:2,3-Wittig rearrangement
4629:1,2-Wittig rearrangement
4469:Parikh–Doering oxidation
4459:Oxygen rebound mechanism
4124:Adkins–Peterson reaction
4016:Yamaguchi esterification
3956:Hegedus indole synthesis
3921:Bartoli indole synthesis
3792:Bamford–Stevens reaction
3708:Weinreb ketone synthesis
3668:Stork enamine alkylation
3443:Knoevenagel condensation
3313:Ferrier carbocyclization
3203:Castro–Stephens coupling
2829:Hammett acidity function
2819:Free-energy relationship
2764:Curtin–Hammett principle
2749:Conformational isomerism
1086:10.1021/acs.oprd.9b00161
712:The first generation (Pd
617:developed by Buchwald).
5768:Knorr pyrrole synthesis
5703:Bucherer–Bergs reaction
5648:Allan–Robinson reaction
5627:Wagner-Jauregg reaction
5419:Ring-closing metathesis
5344:Larock indole synthesis
5324:Knorr pyrrole synthesis
5179:Bucherer–Bergs reaction
5044:Stieglitz rearrangement
5024:Skattebøl rearrangement
4994:Ring-closing metathesis
4854:Group transfer reaction
4819:Favorskii rearrangement
4759:Cornforth rearrangement
4689:Bamberger rearrangement
4594:Wolff–Kishner reduction
4414:Markó–Lam deoxygenation
4309:Fleming–Tamao oxidation
4304:Fischer–Tropsch process
3991:Oxymercuration reaction
3971:Knorr pyrrole synthesis
3797:Barton–Kellogg reaction
3703:Wagner-Jauregg reaction
3623:Ring-closing metathesis
3613:Reimer–Tiemann reaction
3603:Rauhut–Currier reaction
3518:Nef isocyanide reaction
3478:Malonic ester synthesis
3448:Knorr pyrrole synthesis
3383:High dilution principle
3318:Friedel–Crafts reaction
3253:Cross-coupling reaction
3178:Bucherer–Bergs reaction
3163:Blanc chloromethylation
3153:Blaise ketone synthesis
3128:Baylis–Hillman reaction
3123:Barton–Kellogg reaction
3098:Allan–Robinson reaction
3004:Woodward–Hoffmann rules
2739:Charge-transfer complex
1473:10.1351/pac199971081417
1328:10.1007/3-540-45313-x_5
314:sterically unencumbered
5877:Substitution reactions
5733:Feist–Benary synthesis
5507:Bradsher cycloaddition
5477:4+4 Photocycloaddition
5434:Simmons–Smith reaction
5379:Paternò–Büchi reaction
5239:Feist–Benary synthesis
5229:Dieckmann condensation
4979:Pummerer rearrangement
4959:Oxy-Cope rearrangement
4934:Myers allene synthesis
4884:Jacobsen rearrangement
4799:Electrocyclic reaction
4774:Demjanov rearrangement
4729:Buchner ring expansion
4699:Beckmann rearrangement
4679:Aza-Cope rearrangement
4674:Arndt–Eistert reaction
4649:Alkyne zipper reaction
4569:Transfer hydrogenation
4544:Sharpless oxyamination
4519:Selenoxide elimination
4404:Lombardo methylenation
4329:Griesbaum coozonolysis
4239:Corey–Itsuno reduction
4214:Boyland–Sims oxidation
4154:Angeli–Rimini reaction
3802:Boord olefin synthesis
3746:Arndt–Eistert reaction
3738:Homologation reactions
3538:Nitro-Mannich reaction
3453:Kolbe–Schmitt reaction
3263:Cross-coupling partner
3183:Buchner ring expansion
3103:Arndt–Eistert reaction
2869:Kinetic isotope effect
2616:Rearrangement reaction
2403:10.1002/ejoc.201001393
2135:10.1002/anie.200601612
2064:10.1002/anie.200290036
1681:10.1002/anie.200800497
1297:10.1002/anie.199513481
1030:
992:
942:
895:
861:
805:
770:
690:N-heterocyclic carbene
632:
539:
500:
477:
415:
373:
328:
310:electronically neutral
301:using 1 mol% PdCl
45:relies excessively on
5592:Pauson–Khand reaction
5429:Sharpless epoxidation
5384:Pechmann condensation
5264:Friedländer synthesis
5214:Davis–Beirut reaction
5069:Wallach rearrangement
5039:Stevens rearrangement
4974:Pinacol rearrangement
4954:Overman rearrangement
4869:Hofmann rearrangement
4864:Hayashi rearrangement
4829:Ferrier rearrangement
4784:Dimroth rearrangement
4769:Curtius rearrangement
4764:Criegee rearrangement
4744:Claisen rearrangement
4734:Carroll rearrangement
4669:Amadori rearrangement
4659:Allylic rearrangement
4539:Sharpless epoxidation
4274:Dess–Martin oxidation
4199:Bohn–Schmidt reaction
4059:Hofmann rearrangement
3862:Kauffmann olefination
3785:Olefination reactions
3723:Wurtz–Fittig reaction
3558:Palladium–NHC complex
3438:Kauffmann olefination
3393:Homologation reaction
3243:Corey–House synthesis
3223:Claisen rearrangement
3019:Yukawa–Tsuno equation
2979:Swain–Lupton equation
2959:Spherical aromaticity
2894:Möbius–Hückel concept
2679:Aromatic ring current
2641:Substitution reaction
2123:Angew. Chem. Int. Ed.
2051:Angew. Chem. Int. Ed.
1949:Angew. Chem. Int. Ed.
1669:Angew. Chem. Int. Ed.
1585:Angew. Chem. Int. Ed.
1316:Topics in Curr. Chem.
1028:
990:
940:
893:
859:
803:
768:
630:
595:reductive elimination
537:
498:
475:
413:
403:of the aryl bromide.
371:
326:
215:carbon–nitrogen bonds
213:for the synthesis of
5798:Paal–Knorr synthesis
5668:Barton–Zard reaction
5612:Staudinger synthesis
5562:Ketene cycloaddition
5532:Diels–Alder reaction
5512:Cheletropic reaction
5492:Alkyne trimerisation
5374:Paal–Knorr synthesis
5339:Kulinkovich reaction
5314:Jacobsen epoxidation
5234:Diels–Alder reaction
5029:Smiles rearrangement
5019:Sigmatropic reaction
4904:Lossen rearrangement
4754:Corey–Fuchs reaction
4719:Boekelheide reaction
4714:Bergmann degradation
4644:Achmatowicz reaction
4429:Methionine sulfoxide
4229:Clemmensen reduction
4189:Bergmann degradation
4119:Acyloin condensation
4084:Strecker degradation
4039:Bergmann degradation
4006:Ullmann condensation
3872:Peterson olefination
3847:Hydrazone iodination
3827:Elimination reaction
3728:Zincke–Suhl reaction
3648:Sonogashira coupling
3608:Reformatsky reaction
3568:Peterson olefination
3533:Nierenstein reaction
3463:Kulinkovich reaction
3278:Diels–Alder reaction
3238:Corey–Fuchs reaction
3218:Claisen condensation
3088:Alkyne trimerisation
3063:Acyloin condensation
3029:Σ-bishomoaromaticity
2989:Thorpe–Ingold effect
2601:Elimination reaction
991:Aryl ether synthesis
978:Ullmann condensation
5818:Prilezhaev reaction
5803:Pellizzari reaction
5482:(4+3) cycloaddition
5449:Van Leusen reaction
5424:Robinson annulation
5409:Pschorr cyclization
5404:Prilezhaev reaction
5134:Bergman cyclization
5089:Wolff rearrangement
5074:Weerman degradation
4964:Pericyclic reaction
4944:Neber rearrangement
4839:Fries rearrangement
4724:Brook rearrangement
4709:Bergman cyclization
4554:Staudinger reaction
4499:Rosenmund reduction
4489:Reductive amination
4454:Oppenauer oxidation
4244:Corey–Kim oxidation
4219:Cannizzaro reaction
4094:Weerman degradation
4069:Isosaccharinic acid
3981:Mukaiyama hydration
3837:Hofmann elimination
3822:Dehydrohalogenation
3807:Chugaev elimination
3628:Robinson annulation
3573:Pfitzinger reaction
3343:Gattermann reaction
3288:Wulff–Dötz reaction
3268:Dakin–West reaction
3193:Carbonyl allylation
3138:Bergman cyclization
2924:Kennedy J. P. Orton
2844:Hammond's postulate
2814:Flippin–Lodge angle
2784:Electromeric effect
2709:Beta-silicon effect
2694:Baker–Nathan effect
2363:(43): 10770–10771,
2292:(31): 11049–11061,
2164:(43): 13001–13007,
1760:Thomas J. Colacot.
1417:10.1021/ja00121a030
1249:Tetrahedron Letters
1231:10.1021/ja00096a059
1203:10.1021/ja00092a058
1161:Tetrahedron Letters
1146:10.1246/cl.1983.927
914:Ammonia equivalents
744:The development of
521:hydrodehalogenation
244:reductive amination
231:Stephen L. Buchwald
144:Stephen L. Buchwald
5872:Coupling reactions
5567:McCormack reaction
5517:Conia-ene reaction
5349:Madelung synthesis
5139:Biginelli reaction
4929:Mumm rearrangement
4814:Favorskii reaction
4749:Cope rearrangement
4739:Chan rearrangement
4504:Rubottom oxidation
4434:Miyaura borylation
4399:Lipid peroxidation
4394:Lindgren oxidation
4374:Kornblum oxidation
4369:Kolbe electrolysis
4314:Fukuyama reduction
4224:Carbonyl reduction
4074:Marker degradation
3936:Diazonium compound
3926:Boudouard reaction
3905:Carbon-heteroatom
3832:Grieco elimination
3618:Rieche formylation
3563:Passerini reaction
3493:Meerwein arylation
3413:Hydroxymethylation
3308:Favorskii reaction
3208:Chan rearrangement
3143:Biginelli reaction
3068:Aldol condensation
2914:2-Norbornyl cation
2889:Möbius aromaticity
2884:Markovnikov's rule
2779:Effective molarity
2724:Bürgi–Dunitz angle
2714:Bicycloaromaticity
1767:2020-06-02 at the
1725:10.1039/c0sc00331j
1508:10.1055/s-1997-789
1031:
993:
943:
924:benzophenone imine
896:
862:
806:
771:
633:
590:reaction mechanism
540:
501:
478:
416:
401:oxidative addition
374:
329:
5859:
5858:
5855:
5854:
5851:
5850:
5843:Wohl–Aue reaction
5487:6+4 Cycloaddition
5304:Iodolactonization
4624:1,2-rearrangement
4589:Wohl–Aue reaction
4509:Sabatier reaction
4474:Pinnick oxidation
4439:Mozingo reduction
4384:Leuckart reaction
4339:Haloform reaction
4254:Criegee oxidation
4234:Collins oxidation
4184:Benkeser reaction
4179:Bechamp reduction
4149:Andrussow process
4134:Alcohol oxidation
4044:Edman degradation
3951:Haloform reaction
3900:
3899:
3887:Takai olefination
3852:Julia olefination
3678:Takai olefination
3553:Olefin metathesis
3428:Julia olefination
3353:Grignard reaction
3333:Fukuyama coupling
3248:Coupling reaction
3213:Chan–Lam coupling
3083:Alkyne metathesis
3078:Alkane metathesis
2934:Phosphaethynolate
2839:George S. Hammond
2799:Electronic effect
2754:Conjugated system
2636:Stereospecificity
2631:Stereoselectivity
2596:Addition reaction
2585:organic reactions
2498:10.1021/ja074453g
2486:J. Am. Chem. Soc.
2464:10.1021/ja011122+
2452:J. Am. Chem. Soc.
2430:10.1021/ar0201106
2369:10.1021/ja016863p
2357:J. Am. Chem. Soc.
2343:10.1021/ja984321a
2331:J. Am. Chem. Soc.
2298:10.1021/ja903049z
2286:J. Am. Chem. Soc.
2264:10.1021/ol0166808
2258:(21): 3417–3419,
2230:10.1021/ol016333y
2224:(17): 2729–2732,
2198:(36): 6367–6370,
2192:Tetrahedron Lett.
2170:10.1021/ja0717414
2158:J. Am. Chem. Soc.
2129:(39): 6523–6527,
2100:10.1021/ja035483w
2094:(22): 6653–6655,
2088:J. Am. Chem. Soc.
2057:(24): 4746–4748,
2029:10.1021/jo991699y
1996:10.1021/ja981318i
1990:(29): 7369–7370,
1984:J. Am. Chem. Soc.
1955:(16): 2413–2416,
1935:10.1021/ja982250+
1929:(37): 9722–9723,
1923:J. Am. Chem. Soc.
1908:10.1021/ja971583o
1902:(36): 8451–8458,
1895:J. Am. Chem. Soc.
1880:10.1021/jo961930x
1852:10.1021/ja9608306
1839:J. Am. Chem. Soc.
1823:10.1021/ja960937t
1817:(30): 7217–7218,
1811:J. Am. Chem. Soc.
1797:10.1021/jo951844h
1675:(34): 6338–6361,
1634:10.1021/ar800098p
1628:(11): 1534–1544,
1591:(15): 2046–2067,
1568:10.1021/ar9600650
1542:10.1021/ar970282g
1443:10.1021/om9509608
1437:(12): 2755–2763,
1411:(16): 4708–4709,
1405:J. Am. Chem. Soc.
1391:10.1021/ja954121o
1385:(15): 3626–3633,
1379:J. Am. Chem. Soc.
1364:10.1021/ja971057x
1358:(35): 8232–8245,
1352:J. Am. Chem. Soc.
1337:978-3-540-42175-7
1291:(12): 1348–1350,
1256:(21): 3609–3612,
1225:(17): 7901–7902,
1218:J. Am. Chem. Soc.
1197:(13): 5969–5970,
1190:J. Am. Chem. Soc.
1168:(30): 3175–3178,
1134:Chemistry Letters
1046:
1045:
1008:
1007:
958:
957:
911:
910:
877:
876:
821:
820:
786:
785:
648:
647:
555:
554:
493:
492:
431:
430:
389:
388:
344:
343:
268:bond formations.
258:Goldberg reaction
211:chemical reaction
203:organic chemistry
199:
198:
158:Coupling reaction
130:
129:
122:
104:
16:(Redirected from
5889:
5838:Wenker synthesis
5828:Stollé synthesis
5683:Bobbitt reaction
5653:Auwers synthesis
5597:Povarov reaction
5522:Cyclopropanation
5460:
5454:Wenker synthesis
5209:Darzens reaction
5159:Bobbitt reaction
5004:Schmidt reaction
4809:Enyne metathesis
4584:Whiting reaction
4579:Wharton reaction
4524:Shapiro reaction
4514:Sarett oxidation
4479:Prévost reaction
4289:Emde degradation
4099:Wohl degradation
4079:Ruff degradation
4049:Emde degradation
3946:Grignard reagent
3882:Shapiro reaction
3867:McMurry reaction
3734:
3698:Ullmann reaction
3663:Stollé synthesis
3653:Stetter reaction
3643:Shapiro reaction
3633:Sakurai reaction
3528:Negishi coupling
3508:Minisci reaction
3503:Michael reaction
3488:McMurry reaction
3483:Mannich reaction
3363:Hammick reaction
3358:Grignard reagent
3298:Enyne metathesis
3283:Doebner reaction
3273:Darzens reaction
3118:Barbier reaction
3108:Auwers synthesis
3035:
3009:Woodward's rules
2974:Superaromaticity
2964:Spiroaromaticity
2864:Inductive effect
2859:Hyperconjugation
2834:Hammett equation
2774:Edwards equation
2626:Regioselectivity
2577:
2570:
2563:
2554:
2519:
2518:
2509:
2481:
2475:
2474:
2458:(7): 1261–1268,
2447:
2441:
2440:
2413:
2407:
2406:
2386:
2380:
2379:
2352:
2346:
2345:
2325:
2319:
2318:
2309:
2281:
2275:
2274:
2247:
2241:
2240:
2213:
2207:
2206:
2187:
2181:
2180:
2152:
2146:
2145:
2117:
2111:
2110:
2082:
2076:
2075:
2066:
2046:
2040:
2039:
2023:(4): 1158–1174,
2014:
2005:
1999:
1998:
1978:
1972:
1971:
1944:
1938:
1937:
1917:
1911:
1910:
1889:
1883:
1882:
1874:(5): 1268–1273,
1861:
1855:
1854:
1832:
1826:
1825:
1806:
1800:
1799:
1791:(3): 1133–1135,
1778:
1772:
1758:
1752:
1746:
1745:
1736:
1708:
1702:
1701:
1692:
1664:
1655:
1654:
1645:
1617:
1608:
1607:
1580:
1571:
1570:
1551:
1545:
1544:
1525:
1519:
1518:
1491:
1485:
1484:
1475:
1466:(8): 1416–1423,
1460:Pure Appl. Chem.
1455:
1446:
1445:
1426:
1420:
1419:
1400:
1394:
1393:
1373:
1367:
1366:
1347:
1341:
1340:
1311:
1300:
1299:
1278:
1267:
1266:
1265:
1243:
1234:
1233:
1212:
1206:
1205:
1183:
1177:
1176:
1155:
1149:
1148:
1129:
1123:
1122:
1104:
1098:
1097:
1080:(8): 1478–1483.
1069:
1040:
1021:
1002:
983:
952:
933:
905:
886:
871:
852:
815:
796:
780:
761:
735:
725:intermolecularly
673:natural products
642:
623:
549:
530:
487:
468:
455:secondary amines
425:
406:
383:
364:
338:
319:
283:natural products
276:
267:
254:functional group
251:
191:
176:
132:
125:
118:
114:
111:
105:
103:
62:
38:
30:
21:
5897:
5896:
5892:
5891:
5890:
5888:
5887:
5886:
5862:
5861:
5860:
5847:
5748:Gewald reaction
5631:
5458:
5439:Skraup reaction
5274:Graham reaction
5269:Gewald reaction
5100:
5093:
4615:
4608:
4564:Swern oxidation
4549:Stahl oxidation
4494:Riley oxidation
4449:Omega oxidation
4409:Luche reduction
4359:Jones oxidation
4324:Glycol cleavage
4319:Ganem oxidation
4264:Davis oxidation
4259:Dakin oxidation
4194:Birch reduction
4144:Amide reduction
4110:
4103:
4064:Hooker reaction
4026:
4020:
3908:
3906:
3896:
3892:Wittig reaction
3780:
3776:Wittig reaction
3751:Hooker reaction
3732:
3713:Wittig reaction
3688:Thorpe reaction
3673:Suzuki reaction
3658:Stille reaction
3593:Quelet reaction
3468:Kumada coupling
3418:Ivanov reaction
3408:Hydrovinylation
3388:Hiyama coupling
3348:Glaser coupling
3158:Blaise reaction
3148:Bingel reaction
3133:Benary reaction
3050:
3048:
3042:
3033:
2929:Passive binding
2849:Homoaromaticity
2699:Baldwin's rules
2674:Antiaromaticity
2669:Anomeric effect
2645:
2587:
2581:
2527:
2522:
2483:
2482:
2478:
2449:
2448:
2444:
2418:Acc. Chem. Res.
2415:
2414:
2410:
2388:
2387:
2383:
2354:
2353:
2349:
2327:
2326:
2322:
2283:
2282:
2278:
2249:
2248:
2244:
2215:
2214:
2210:
2189:
2188:
2184:
2154:
2153:
2149:
2119:
2118:
2114:
2084:
2083:
2079:
2048:
2047:
2043:
2012:
2007:
2006:
2002:
1980:
1979:
1975:
1946:
1945:
1941:
1919:
1918:
1914:
1891:
1890:
1886:
1863:
1862:
1858:
1834:
1833:
1829:
1808:
1807:
1803:
1780:
1779:
1775:
1769:Wayback Machine
1759:
1755:
1749:
1710:
1709:
1705:
1666:
1665:
1658:
1622:Acc. Chem. Res.
1619:
1618:
1611:
1582:
1581:
1574:
1556:Acc. Chem. Res.
1553:
1552:
1548:
1530:Acc. Chem. Res.
1527:
1526:
1522:
1493:
1492:
1488:
1457:
1456:
1449:
1431:Organometallics
1428:
1427:
1423:
1402:
1401:
1397:
1375:
1374:
1370:
1349:
1348:
1344:
1338:
1313:
1312:
1303:
1280:
1279:
1270:
1245:
1244:
1237:
1214:
1213:
1209:
1185:
1184:
1180:
1157:
1156:
1152:
1131:
1130:
1126:
1119:
1106:
1105:
1101:
1071:
1070:
1066:
1062:
1038:
1013:
1000:
966:
950:
916:
903:
869:
826:
813:
778:
742:
715:
710:
685:
677:total syntheses
669:
661:
640:
586:
547:
485:
444:
440:
423:
398:
381:
359:
355:
336:
307:
304:
295:
287:total syntheses
265:
247:
235:John F. Hartwig
187:
172:
148:John F. Hartwig
146:
126:
115:
109:
106:
63:
61:
55:
51:primary sources
39:
28:
23:
22:
15:
12:
11:
5:
5895:
5893:
5885:
5884:
5882:Name reactions
5879:
5874:
5864:
5863:
5857:
5856:
5853:
5852:
5849:
5848:
5846:
5845:
5840:
5835:
5830:
5825:
5820:
5815:
5810:
5805:
5800:
5795:
5790:
5785:
5780:
5775:
5770:
5765:
5760:
5755:
5753:Hantzsch ester
5750:
5745:
5740:
5735:
5730:
5725:
5720:
5715:
5710:
5705:
5700:
5695:
5690:
5685:
5680:
5675:
5670:
5665:
5663:Banert cascade
5660:
5655:
5650:
5645:
5639:
5637:
5633:
5632:
5630:
5629:
5624:
5619:
5614:
5609:
5604:
5602:Prato reaction
5599:
5594:
5589:
5584:
5579:
5574:
5569:
5564:
5559:
5554:
5549:
5544:
5539:
5534:
5529:
5524:
5519:
5514:
5509:
5504:
5499:
5494:
5489:
5484:
5479:
5474:
5468:
5466:
5457:
5456:
5451:
5446:
5441:
5436:
5431:
5426:
5421:
5416:
5411:
5406:
5401:
5396:
5391:
5386:
5381:
5376:
5371:
5366:
5361:
5356:
5351:
5346:
5341:
5336:
5331:
5326:
5321:
5316:
5311:
5306:
5301:
5296:
5291:
5286:
5281:
5276:
5271:
5266:
5261:
5256:
5251:
5246:
5241:
5236:
5231:
5226:
5221:
5216:
5211:
5206:
5201:
5196:
5191:
5186:
5181:
5176:
5171:
5166:
5161:
5156:
5151:
5146:
5141:
5136:
5131:
5126:
5121:
5116:
5111:
5105:
5103:
5095:
5094:
5092:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4966:
4961:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4861:
4856:
4851:
4846:
4841:
4836:
4831:
4826:
4821:
4816:
4811:
4806:
4801:
4796:
4791:
4786:
4781:
4776:
4771:
4766:
4761:
4756:
4751:
4746:
4741:
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4694:Banert cascade
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4620:
4618:
4614:Rearrangement
4610:
4609:
4607:
4606:
4604:Zinin reaction
4601:
4596:
4591:
4586:
4581:
4576:
4574:Wacker process
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4386:
4381:
4376:
4371:
4366:
4361:
4356:
4351:
4349:Hydrogenolysis
4346:
4341:
4336:
4331:
4326:
4321:
4316:
4311:
4306:
4301:
4299:Étard reaction
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4251:
4246:
4241:
4236:
4231:
4226:
4221:
4216:
4211:
4206:
4204:Bosch reaction
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4115:
4113:
4109:Organic redox
4105:
4104:
4102:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4030:
4028:
4022:
4021:
4019:
4018:
4013:
4008:
4003:
3998:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3958:
3953:
3948:
3943:
3941:Esterification
3938:
3933:
3928:
3923:
3918:
3912:
3910:
3902:
3901:
3898:
3897:
3895:
3894:
3889:
3884:
3879:
3874:
3869:
3864:
3859:
3854:
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3788:
3786:
3782:
3781:
3779:
3778:
3773:
3768:
3763:
3758:
3753:
3748:
3742:
3740:
3731:
3730:
3725:
3720:
3718:Wurtz reaction
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3588:Prins reaction
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3403:Hydrocyanation
3400:
3395:
3390:
3385:
3380:
3375:
3373:Henry reaction
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3220:
3215:
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3073:Aldol reaction
3070:
3065:
3060:
3054:
3052:
3047:Carbon-carbon
3044:
3043:
3038:
3032:
3031:
3026:
3024:Zaitsev's rule
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2971:
2969:Steric effects
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2666:
2661:
2656:
2650:
2647:
2646:
2644:
2643:
2638:
2633:
2628:
2623:
2621:Redox reaction
2618:
2613:
2608:
2606:Polymerization
2603:
2598:
2592:
2589:
2588:
2582:
2580:
2579:
2572:
2565:
2557:
2551:
2550:
2542:
2533:
2526:
2525:External links
2523:
2521:
2520:
2492:(1): 195–200,
2476:
2442:
2424:(4): 234–245,
2408:
2381:
2347:
2320:
2276:
2242:
2208:
2182:
2147:
2112:
2077:
2041:
2000:
1973:
1939:
1912:
1884:
1856:
1827:
1801:
1773:
1753:
1747:
1703:
1656:
1609:
1572:
1546:
1520:
1502:(4): 329–340,
1486:
1447:
1421:
1395:
1368:
1342:
1336:
1301:
1268:
1235:
1207:
1178:
1150:
1140:(6): 927–928,
1124:
1117:
1099:
1063:
1061:
1058:
1044:
1043:
1034:
1032:
1011:
1006:
1005:
996:
994:
965:
962:
956:
955:
946:
944:
915:
912:
909:
908:
899:
897:
875:
874:
865:
863:
825:
822:
819:
818:
809:
807:
784:
783:
774:
772:
741:
738:
737:
736:
721:intramolecular
713:
709:
706:
684:
681:
668:
665:
659:
646:
645:
636:
634:
585:
582:
553:
552:
543:
541:
491:
490:
481:
479:
442:
438:
435:transamination
429:
428:
419:
417:
396:
387:
386:
377:
375:
357:
353:
342:
341:
332:
330:
305:
302:
294:
291:
278:
277:
197:
196:
193:
192:
185:
178:
177:
170:
166:
165:
161:
160:
155:
154:Reaction type
151:
150:
141:
137:
136:
128:
127:
42:
40:
33:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5894:
5883:
5880:
5878:
5875:
5873:
5870:
5869:
5867:
5844:
5841:
5839:
5836:
5834:
5831:
5829:
5826:
5824:
5821:
5819:
5816:
5814:
5811:
5809:
5806:
5804:
5801:
5799:
5796:
5794:
5791:
5789:
5786:
5784:
5781:
5779:
5776:
5774:
5771:
5769:
5766:
5764:
5763:Herz reaction
5761:
5759:
5756:
5754:
5751:
5749:
5746:
5744:
5741:
5739:
5736:
5734:
5731:
5729:
5726:
5724:
5721:
5719:
5716:
5714:
5711:
5709:
5706:
5704:
5701:
5699:
5696:
5694:
5691:
5689:
5686:
5684:
5681:
5679:
5676:
5674:
5671:
5669:
5666:
5664:
5661:
5659:
5656:
5654:
5651:
5649:
5646:
5644:
5641:
5640:
5638:
5634:
5628:
5625:
5623:
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5603:
5600:
5598:
5595:
5593:
5590:
5588:
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5565:
5563:
5560:
5558:
5555:
5553:
5550:
5548:
5545:
5543:
5540:
5538:
5535:
5533:
5530:
5528:
5525:
5523:
5520:
5518:
5515:
5513:
5510:
5508:
5505:
5503:
5500:
5498:
5495:
5493:
5490:
5488:
5485:
5483:
5480:
5478:
5475:
5473:
5470:
5469:
5467:
5465:
5464:Cycloaddition
5461:
5455:
5452:
5450:
5447:
5445:
5442:
5440:
5437:
5435:
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5412:
5410:
5407:
5405:
5402:
5400:
5397:
5395:
5392:
5390:
5387:
5385:
5382:
5380:
5377:
5375:
5372:
5370:
5367:
5365:
5362:
5360:
5357:
5355:
5352:
5350:
5347:
5345:
5342:
5340:
5337:
5335:
5332:
5330:
5327:
5325:
5322:
5320:
5317:
5315:
5312:
5310:
5309:Isay reaction
5307:
5305:
5302:
5300:
5297:
5295:
5292:
5290:
5287:
5285:
5282:
5280:
5277:
5275:
5272:
5270:
5267:
5265:
5262:
5260:
5257:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5230:
5227:
5225:
5222:
5220:
5217:
5215:
5212:
5210:
5207:
5205:
5204:Cycloaddition
5202:
5200:
5197:
5195:
5192:
5190:
5187:
5185:
5182:
5180:
5177:
5175:
5172:
5170:
5167:
5165:
5162:
5160:
5157:
5155:
5152:
5150:
5147:
5145:
5142:
5140:
5137:
5135:
5132:
5130:
5127:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5106:
5104:
5102:
5099:Ring forming
5096:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4999:Rupe reaction
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4860:
4857:
4855:
4852:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4625:
4622:
4621:
4619:
4617:
4611:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4389:Ley oxidation
4387:
4385:
4382:
4380:
4377:
4375:
4372:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4354:Hydroxylation
4352:
4350:
4347:
4345:
4344:Hydrogenation
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4279:DNA oxidation
4277:
4275:
4272:
4270:
4269:Deoxygenation
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4160:
4159:Aromatization
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4116:
4114:
4112:
4106:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4031:
4029:
4023:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3996:Reed reaction
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3942:
3939:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3913:
3911:
3907:bond forming
3903:
3893:
3890:
3888:
3885:
3883:
3880:
3878:
3875:
3873:
3870:
3868:
3865:
3863:
3860:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3812:Cope reaction
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3789:
3787:
3783:
3777:
3774:
3772:
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3743:
3741:
3739:
3735:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3523:Nef synthesis
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3498:Methylenation
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3368:Heck reaction
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3055:
3053:
3049:bond forming
3045:
3041:
3036:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3014:Y-aromaticity
3012:
3010:
3007:
3005:
3002:
3000:
2999:Walsh diagram
2997:
2995:
2992:
2990:
2987:
2985:
2984:Taft equation
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2954:Σ-aromaticity
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2879:Marcus theory
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2854:Hückel's rule
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2809:Evelyn effect
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2789:Electron-rich
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2704:Bema Hapothle
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2651:
2648:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2594:
2593:
2590:
2586:
2578:
2573:
2571:
2566:
2564:
2559:
2558:
2555:
2549:
2546:
2543:
2541:
2537:
2534:
2532:
2529:
2528:
2524:
2517:
2513:
2508:
2503:
2499:
2495:
2491:
2487:
2480:
2477:
2473:
2469:
2465:
2461:
2457:
2453:
2446:
2443:
2439:
2435:
2431:
2427:
2423:
2419:
2412:
2409:
2404:
2400:
2396:
2392:
2385:
2382:
2378:
2374:
2370:
2366:
2362:
2358:
2351:
2348:
2344:
2340:
2337:: 3224–3225,
2336:
2332:
2324:
2321:
2317:
2313:
2308:
2303:
2299:
2295:
2291:
2287:
2280:
2277:
2273:
2269:
2265:
2261:
2257:
2253:
2246:
2243:
2239:
2235:
2231:
2227:
2223:
2219:
2212:
2209:
2205:
2201:
2197:
2193:
2186:
2183:
2179:
2175:
2171:
2167:
2163:
2159:
2151:
2148:
2144:
2140:
2136:
2132:
2128:
2124:
2116:
2113:
2109:
2105:
2101:
2097:
2093:
2089:
2081:
2078:
2074:
2070:
2065:
2060:
2056:
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348:Dale L. Boger
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71: –
70:
66:
65:Find sources:
59:
53:
52:
48:
43:This article
41:
37:
32:
31:
19:
4804:Ene reaction
4164:Autoxidation
4025:Degradation
3916:Azo coupling
3693:Ugi reaction
3293:Ene reaction
3093:Alkynylation
2944:Polyfluorene
2939:Polar effect
2804:Electrophile
2719:Bredt's rule
2689:Baird's rule
2659:Alpha effect
2544:
2535:
2489:
2485:
2479:
2455:
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2417:
2411:
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2150:
2126:
2122:
2115:
2091:
2087:
2080:
2054:
2050:
2044:
2020:
2016:
2003:
1987:
1983:
1976:
1952:
1948:
1942:
1926:
1922:
1915:
1899:
1893:
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1871:
1865:
1859:
1843:
1837:
1830:
1814:
1810:
1804:
1788:
1782:
1776:
1756:
1750:
1719:(1): 27–50,
1716:
1712:
1706:
1672:
1668:
1625:
1621:
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1584:
1559:
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753:
748:(BINAP) and
743:
718:
711:
686:
670:
657:
649:
638:
619:
603:
587:
556:
545:
502:
483:
451:diethylamine
445:followed by
432:
421:
414:hartwig 1994
390:
379:
345:
334:
296:
279:
227:aryl halides
206:
200:
189:RXNO:0000192
184:ontology ID
164:Identifiers
140:Named after
116:
107:
97:
90:
83:
76:
64:
44:
3303:Ethenolysis
2949:Ring strain
2919:Nucleophile
2744:Clar's rule
2684:Aromaticity
1562:: 805–818,
1536:: 852–860,
1322:: 131–209,
694:bite angles
667:Application
652:equilibrium
607:monodentate
110:August 2016
5866:Categories
5587:Ozonolysis
5114:Annulation
4464:Ozonolysis
2583:Topics in
2252:Org. Lett.
2218:Org. Lett.
1713:Chem. Sci.
1118:0471937495
1060:References
395:complex Pd
80:newspapers
47:references
5101:reactions
4616:reactions
4111:reactions
4027:reactions
3909:reactions
3051:reactions
2397:: 53–57.
1516:196704196
1094:198366762
847:ferrocene
839:phosphate
835:carbonate
831:hydroxide
790:chelation
611:chelating
601:product.
584:Mechanism
574:triflates
570:chlorides
559:phosphine
525:Mechanism
517:organotin
346:In 1984,
2994:Vinylogy
2664:Annulene
2611:Reagents
2516:18076166
2472:11841295
2438:12693921
2377:11674023
2316:19591470
2272:11594848
2238:11506620
2178:17918833
2143:16955526
2108:12769573
2073:12481346
2037:10814067
1969:10458806
1765:Archived
1743:22432049
1699:18663711
1652:18681463
1605:29711045
1482:34700080
970:alcohols
702:Spanphos
698:Xantphos
696:such as
459:anilines
217:via the
2654:A value
2507:2551326
2307:2823124
1734:3306613
1690:3517088
1643:2819174
1496:Synlett
928:aniline
919:Ammonia
566:iodides
562:ligands
527:below)
293:History
94:scholar
2514:
2504:
2470:
2436:
2375:
2314:
2304:
2270:
2236:
2176:
2141:
2106:
2071:
2035:
1967:
1741:
1731:
1697:
1687:
1650:
1640:
1603:
1514:
1480:
1334:
1115:
1092:
1054:nickel
1050:copper
974:ethers
837:, and
572:, and
513:LiHMDS
509:NaOtBu
352:Pd(PPh
223:amines
205:, the
96:
89:
82:
75:
67:
2013:(PDF)
1512:S2CID
1478:S2CID
1090:S2CID
1039:Eq.14
1001:Eq.13
951:Eq.12
904:Eq.11
870:Eq.10
683:Scope
599:imine
578:Scope
463:ortho
447:argon
441:SnNEt
437:of Bu
225:with
209:is a
101:JSTOR
87:books
2548:Link
2540:Link
2512:PMID
2468:PMID
2434:PMID
2395:2011
2373:PMID
2312:PMID
2268:PMID
2234:PMID
2174:PMID
2139:PMID
2104:PMID
2069:PMID
2033:PMID
1965:PMID
1739:PMID
1695:PMID
1648:PMID
1601:PMID
1500:1997
1332:ISBN
1113:ISBN
1052:and
814:Eq.9
788:The
779:Eq.8
755:JACS
700:and
641:Eq.7
588:The
548:Eq.6
505:base
486:Eq.5
424:Eq.4
382:Eq.3
337:Eq.2
233:and
73:news
2502:PMC
2494:doi
2490:130
2460:doi
2456:124
2426:doi
2399:doi
2365:doi
2361:123
2339:doi
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2302:PMC
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2260:doi
2226:doi
2200:doi
2166:doi
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1992:doi
1988:120
1957:doi
1931:doi
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1900:119
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1729:PMC
1721:doi
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1320:219
1293:doi
1258:doi
1227:doi
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1199:doi
1195:116
1170:doi
1142:doi
1082:doi
609:or
299:tin
266:C−N
249:C−N
221:of
201:In
182:RSC
49:to
5868::
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2500:,
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2019:,
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