181:
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761:
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compounds are generally stable towards water and air. Palladium catalysts can be problematic for the pharmaceutical industry, which faces extensive regulation regarding heavy metals. Many pharmaceutical chemists attempt to use coupling reactions early in production to minimize metal traces in the
99:
Many mechanisms exist reflecting the myriad types of cross-couplings, including those that do not require metal catalysts. Often, however, cross-coupling refers to a metal-catalyzed reaction of a nucleophilic partner with an electrophilic partner.
1813:
Murahashi, Shunichi; Yamamura, Masaaki; Yanagisawa, Kenichi; Mita, Nobuaki; Kondo, Kaoru (1979). "Stereoselective synthesis of alkenes and alkenyl sulfides from alkenyl halides using palladium and ruthenium catalysts".
171:
of the two coupling fragments to regenerate the catalyst and give the organic product. Unsaturated substrates, such as C(sp)âX and C(sp)âX bonds, couple more easily, in part because they add readily to the catalyst.
1911:
Jennifer X. Qiao; Patrick Y.S. Lam (2011). "Recent
Advances in ChanâLam Coupling Reaction: Copper-Promoted CâHeteroatom Bond Cross-Coupling Reactions with Boronic Acids and Derivatives". In Dennis G. Hall (ed.).
1448:
Johansson
Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (2012). "Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize".
5246:
1629:
Evano, Gwilherm; Blanchard, Nicolas; Toumi, Mathieu (2008). "Copper-Mediated
Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis".
4362:
1245:
Yi, Hong; Zhang, Guoting; Wang, Huamin; Huang, Zhiyuan; Wang, Jue; Singh, Atul K.; Lei, Aiwen (2017). "Recent
Advances in Radical CâH Activation/Radical Cross-Coupling".
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5400:
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4172:
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960:
Fortman, George C.; Nolan, Steven P. (2011). "N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union".
42:
where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal
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4817:
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4907:
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leaving groups are required for acceptable rates. The main group metal in the organometallic partner usually is an electropositive element such as
4662:
2024:
Roughley, Stephen D.; Jordan, Allan M. (2011). "The
Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates".
2129:
1136:
Roglans, Anna; Pla-Quintana, Anna; Moreno-Mañas, Marcial (2006). "Diazonium Salts as
Substrates in Palladium-Catalyzed Cross-Coupling Reactions".
3494:
5140:
4597:
239:
have been used. Chloride is an ideal group due to the low cost of organochlorine compounds. Frequently, however, CâCl bonds are too inert, and
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Rosen, Brad M.; Quasdorf, Kyle W.; Wilson, Daniella A.; Zhang, Na; Resmerita, Ana-Maria; Garg, Neil K.; Percec, Virgil (2011).
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1028:"Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners"
704:
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1945:
M. Lafrance; C. N. Rowley; T. K. Woo; K. Fagnou (2006). "Catalytic
Intermolecular Direct Arylation of Perfluorobenzenes".
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2277:
2252:
2058:
Hartwig, J. F. Organotransition Metal
Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010.
1664:
Robin B. Bedford (2015). "How Low Does Iron Go? Chasing the Active
Species in Fe-Catalyzed Cross-Coupling Reactions".
1069:
MolnĂĄr, ĂrpĂĄd (2011). "Efficient, Selective, and
Recyclable Palladium Catalysts in CarbonâCarbon Coupling Reactions".
5251:
4952:
4757:
4192:
3757:
3732:
3672:
3264:
2971:
2621:
1991:
Cornils, Boy; Börner, Armin; Franke, Robert; Zhang, Baoxin; Wiebus, Ernst; Schmid, Klaus (2017). "Hydroformylation".
2806:
1394:
King, A. O.; Yasuda, N. (2004). "Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals".
760:
4542:
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3717:
3241:
3076:
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2537:
2497:
2242:
1551:
Yin, L.; Liebscher, J. (2007). "CarbonâCarbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts".
989:
Yin; Liebscher, JĂŒrgen (2007). "CarbonâCarbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts".
348:
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88:
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749:
Many cross-couplings entail forming carbonâheteroatom bonds (heteroatom = S, N, O). A popular method is the
5286:
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2362:
2139:
2134:
1955:
1114:
1102:
202:
84:
5361:
4107:
2731:
1788:
950:. with Suzuki coupling being most widely used. Some polymers and monomers are also prepared in this way.
871:
4947:
4902:
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2159:
494:
168:
128:
2407:
2402:
1594:
Corbet, Jean-Pierre; Mignani, GĂ©rard (2006). "Selected Patented Cross-Coupling Reaction Technologies".
1337:
Corbet, Jean-Pierre; Mignani, GĂ©rard (2006). "Selected Patented Cross-Coupling Reaction Technologies".
5000:
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103:
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2004:
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1006:
977:
930:
Cross-coupling reactions are important for the production of pharmaceuticals, examples being
613:
208:
Copper-based catalysts are also common, especially for coupling involving heteroatom-C bonds.
70:
39:
31:
5356:
5201:
5171:
5115:
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1996:
1965:
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1078:
1047:
1039:
998:
969:
738:
467:
193:
164:
136:
1398:. Topics in Organometallic Chemistry. Vol. 6. Heidelberg: Springer. pp. 205â245.
5266:
4957:
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4012:
3967:
3927:
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2447:
2367:
2192:
2187:
1527:
582:
524:
384:
197:
108:
80:
76:
2237:
2207:
1914:
Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials
5271:
5181:
5120:
4212:
4122:
4092:
3867:
3722:
3459:
3236:
3106:
2921:
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2124:
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1863:
1760:
1735:
1314:
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1052:
1027:
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4827:
4722:
4517:
3907:
3872:
3862:
3797:
3787:
3677:
3514:
3330:
3041:
3016:
2886:
2532:
2517:
2502:
2397:
2327:
2307:
2222:
1491:
Sun, Chang-Liang; Shi, Zhang-Jie (2014). "Transition-Metal-Free Coupling Reactions".
1098:
911:
411:
220:
1580:
1477:
1428:"The Nobel Prize in Chemistry 2010 - Richard F. Heck, Ei-ichi Negishi, Akira Suzuki"
1018:
4322:
3682:
3434:
3211:
2811:
2611:
2462:
2457:
2322:
2177:
1699:
Cahiez, GĂ©Rard; Moyeux, Alban (2010). "Cobalt-Catalyzed Cross-Coupling Reactions".
1216:
Cahiez, GĂ©rard; Moyeux, Alban (2010). "Cobalt-Catalyzed Cross-Coupling Reactions".
1165:
236:
1677:
1105:(1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds".
192:
Catalysts are often based on palladium, which is frequently selected due to high
2821:
2467:
2437:
2202:
1879:
1784:
1305:
1258:
1190:
947:
943:
931:
5105:
4632:
3982:
2071:
2000:
1921:
935:
152:
1835:
376:
2045:
1977:
1897:
1769:
1720:
1685:
1650:
1615:
1572:
1512:
1469:
1461:
1358:
1323:
1266:
1237:
1208:
1157:
1090:
1061:
1010:
981:
69:
but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of
27:
Chemical reaction in which two molecules are joined due to a metal catalyst
2512:
2182:
939:
232:
228:
43:
17:
1827:
1128:
2172:
973:
240:
2037:
1969:
1751:
1712:
1642:
1607:
1564:
1504:
1350:
1229:
1149:
1082:
1043:
1002:
244:
224:
143:
MR(R') is formed in a two step process from a low valence precursor L
112:
58:
1403:
914:
with fluorinated arene. The process is unusual in that it involves
211:
Iron-, cobalt-, and nickel-based catalysts have been investigated.
1864:"Applications of Palladium-Catalyzed CâN Cross-Coupling Reactions"
256:
179:
102:
1790:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
1736:"Nickel-Catalyzed Cross-Couplings Involving CarbonâOxygen Bonds"
668:
252:
116:
54:
2556:
2075:
1852:, 2nd ed.; Oxford UP: Oxford, U.K., 2012. pp. 1069-1102.
248:
759:
1993:
Applied Homogeneous Catalysis with Organometallic Compounds
1793:(6th ed.), New York: Wiley-Interscience, p. 792,
1026:
Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S. (2011).
267:
Many cross-couplings entail forming carbonâcarbon bonds.
737:
The restrictions on carbon atom geometry mainly inhibit
782:
269:
91:
for developing palladium-catalyzed coupling reactions.
1372:
New Trends in Cross-Coupling: Theory and Applications
5247:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
5154:
4981:
4616:
4131:
3626:
3543:
3423:
3303:
3255:
2565:
163:MR(X). Subsequently, the second partner undergoes
4308:Divinylcyclopropane-cycloheptadiene rearrangement
57:; M = main group center such as Li or MgX; X =
4568:Thermal rearrangement of aromatic hydrocarbons
3202:Thermal rearrangement of aromatic hydrocarbons
1290:"Cross-Coupling of Heteroatomic Electrophiles"
1288:Korch, Katerina M.; Watson, Donald A. (2019).
1175:"Cross-Coupling of Heteroatomic Electrophiles"
1173:Korch, Katerina M.; Watson, Donald A. (2019).
5297:Lectka enantioselective beta-lactam synthesis
2087:
636:see LiebeskindâSrogl coupling, gives ketones
8:
5076:Inverse electron-demand DielsâAlder reaction
2897:Heterogeneous metal catalyzed cross-coupling
4418:Lobry de BruynâVan Ekenstein transformation
1862:Ruiz-Castillo, P.; Buchwald, S. L. (2016).
4978:
3252:
2553:
2094:
2080:
2072:
910:Palladium-catalyzes the cross-coupling of
4908:Petrenko-Kritschenko piperidone synthesis
4363:FritschâButtenbergâWiechell rearrangement
1959:
1887:
1759:
1313:
1198:
1118:
1051:
5071:Intramolecular DielsâAlder cycloaddition
1389:
1387:
1450:Angewandte Chemie International Edition
1280:
167:with a source of R'. The final step is
46:. One important reaction type is this:
5091:Metal-centered cycloaddition reactions
4743:DebusâRadziszewski imidazole synthesis
2687:BodrouxâChichibabin aldehyde synthesis
794:
791:
281:
278:
223:X in the organic partner is usually a
5237:Diazoalkane 1,3-dipolar cycloaddition
5141:Vinylcyclopropane (5+2) cycloaddition
5046:Diazoalkane 1,3-dipolar cycloaddition
4818:HurdâMori 1,2,3-thiadiazole synthesis
4313:DowdâBeckwith ring-expansion reaction
3480:HurdâMori 1,2,3-thiadiazole synthesis
2393:LFER solvent coefficients (data page)
1848:Clayden, J.; Greeves, N.; Warren, S.
205:based on Pd are also well developed.
7:
5401:Carbon-carbon bond forming reactions
4048:Sharpless asymmetric dihydroxylation
3285:Methoxymethylenetriphenylphosphorane
1396:Organometallics in Process Chemistry
755:
699:requires oxidant or dehydrogenation
53:(R, R' = organic fragments, usually
4173:AllenâMillarâTrippett rearrangement
5312:Nitrone-olefin (3+2) cycloaddition
5307:Niementowski quinazoline synthesis
5096:Nitrone-olefin (3+2) cycloaddition
5021:Azide-alkyne Huisgen cycloaddition
4883:Niementowski quinazoline synthesis
4638:Azide-alkyne Huisgen cycloaddition
3943:MeerweinâPonndorfâVerley reduction
3495:LeimgruberâBatcho indole synthesis
25:
5136:Trimethylenemethane cycloaddition
4838:JohnsonâCoreyâChaykovsky reaction
4703:CadoganâSundberg indole synthesis
4683:BohlmannâRahtz pyridine synthesis
4643:BaeyerâEmmerling indole synthesis
3450:CadoganâSundberg indole synthesis
2942:JohnsonâCoreyâChaykovsky reaction
65:These reactions are used to form
5232:CookâHeilbron thiazole synthesis
5061:Hexadehydro DielsâAlder reaction
4888:Niementowski quinoline synthesis
4718:CookâHeilbron thiazole synthesis
4663:BischlerâMöhlau indole synthesis
4573:TiffeneauâDemjanov rearrangement
4203:BakerâVenkataraman rearrangement
3361:HornerâWadsworthâEmmons reaction
3032:Mizoroki-Heck vs. Reductive Heck
2917:HornerâWadsworthâEmmons reaction
2428:Neighbouring group participation
1816:The Journal of Organic Chemistry
741:when complexed to the catalyst.
4768:Fiesselmann thiophene synthesis
4598:WestphalenâLettrĂ© rearrangement
4578:Vinylcyclopropane rearrangement
4408:KornblumâDeLaMare rearrangement
4053:Epoxidation of allylic alcohols
3963:Noyori asymmetric hydrogenation
3898:KornblumâDeLaMare rearrangement
3573:GallagherâHollander degradation
1916:. Wiley-VCH. pp. 315â361.
1532:Chemical & Engineering News
5227:Chichibabin pyridine synthesis
4713:Chichibabin pyridine synthesis
4673:BlumâIttah aziridine synthesis
4508:Ring expansion and contraction
2777:Cross dehydrogenative coupling
2026:Journal of Medicinal Chemistry
824:Ar-X (X = OAr, N(H)Ar, SR, CN)
705:Decarboxylative cross-coupling
677:Cross dehydrogenative coupling
1:
5197:BischlerâNapieralski reaction
5155:Heterocycle forming reactions
4808:Hemetsberger indole synthesis
4668:BischlerâNapieralski reaction
4583:WagnerâMeerwein rearrangement
4553:SommeletâHauser rearrangement
4533:SeyferthâGilbert homologation
4398:IrelandâClaisen rearrangement
4393:HofmannâMartius rearrangement
4153:2,3-sigmatropic rearrangement
3768:CoreyâWinter olefin synthesis
3693:BartonâMcCombie deoxygenation
3336:CoreyâWinter olefin synthesis
3290:SeyferthâGilbert homologation
3157:SeyferthâGilbert homologation
1374:Thomas Colacot (Editor) 2014
866:second generation free amine
764:The BuchwaldâHartwig reaction
235:, pivalate esters, and other
5302:LehmstedtâTanasescu reaction
5262:GabrielâColman rearrangement
5217:Bucherer carbazole synthesis
5212:BorscheâDrechsel cyclization
5192:Bernthsen acridine synthesis
5177:Bamberger triazine synthesis
5162:AlgarâFlynnâOyamada reaction
4873:Nazarov cyclization reaction
4738:De Kimpe aziridine synthesis
4693:Bucherer carbazole synthesis
4688:BorscheâDrechsel cyclization
4458:Nazarov cyclization reaction
4438:MeyerâSchuster rearrangement
4368:GabrielâColman rearrangement
4118:WolffensteinâBöters reaction
4003:Reduction of nitro compounds
3853:Grundmann aldehyde synthesis
3658:AlgarâFlynnâOyamada reaction
3067:Olefin conversion technology
3062:NozakiâHiyamaâKishi reaction
2857:GabrielâColman rearrangement
2747:Claisen-Schmidt condensation
2692:Bouveault aldehyde synthesis
1678:10.1021/acs.accounts.5b00042
1430:. NobelPrize.org. 2010-10-06
263:Carbonâcarbon cross-coupling
51:RâM + R'âX â RâR' + MX
5277:Hantzsch pyridine synthesis
5056:Enoneâalkene cycloadditions
4878:Nenitzescu indole synthesis
4798:Hantzsch pyridine synthesis
4763:FerrarioâAckermann reaction
4413:Kowalski ester homologation
4378:Halogen dance rearrangement
4223:Benzilic acid rearrangement
3648:Akabori amino-acid reaction
3608:Von Braun amide degradation
3553:BarbierâWieland degradation
3505:Nenitzescu indole synthesis
3485:KharaschâSosnovsky reaction
3376:JuliaâKocienski olefination
3280:Kowalski ester homologation
2977:Kowalski ester homologation
2952:JuliaâKocienski olefination
2707:CadiotâChodkiewicz coupling
2632:Aza-BaylisâHillman reaction
2577:Acetoacetic ester synthesis
2288:Dynamic binding (chemistry)
2278:Conrotatory and disrotatory
2253:Charge remote fragmentation
1880:10.1021/acs.chemrev.6b00512
1306:10.1021/acs.chemrev.8b00628
1259:10.1021/acs.chemrev.6b00620
1191:10.1021/acs.chemrev.8b00628
731:Requires little-to-no base
294:CadiotâChodkiewicz coupling
184:Mechanism proposed for the
5422:
5342:RobinsonâGabriel synthesis
5292:Kröhnke pyridine synthesis
5126:Retro-DielsâAlder reaction
5066:Imine DielsâAlder reaction
4853:Kröhnke pyridine synthesis
4468:NewmanâKwart rearrangement
4443:MislowâEvans rearrangement
4353:FischerâHepp rearrangement
4298:Di-Ï-methane rearrangement
4078:Stephen aldehyde synthesis
3813:EschweilerâClarke reaction
3530:Williamson ether synthesis
2847:FujiwaraâMoritani reaction
2752:Combes quinoline synthesis
2717:Carbonyl olefin metathesis
2418:More O'FerrallâJencks plot
2343:GrunwaldâWinstein equation
2313:Electron-withdrawing group
2248:Catalytic resonance theory
1526:Thayer, Ann (2005-09-05).
745:Carbonâheteroatom coupling
5352:Urech hydantoin synthesis
5332:PomeranzâFritsch reaction
5257:Fischer oxazole synthesis
4991:1,3-Dipolar cycloaddition
4963:Urech hydantoin synthesis
4933:Reissert indole synthesis
4918:PomeranzâFritsch reaction
4848:Knorr quinoline synthesis
4778:Fischer oxazole synthesis
4708:Camps quinoline synthesis
4628:1,3-Dipolar cycloaddition
4528:Semipinacol rearrangement
4503:RambergâBĂ€cklund reaction
4488:Piancatelli rearrangement
4428:McFadyenâStevens reaction
4183:Alpha-ketol rearrangement
3938:McFadyenâStevens reaction
3883:KilianiâFischer synthesis
3803:Elbs persulfate oxidation
3728:BouveaultâBlanc reduction
3688:BaeyerâVilliger oxidation
3520:SchottenâBaumann reaction
3396:RambergâBĂ€cklund reaction
3275:KilianiâFischer synthesis
3117:RambergâBĂ€cklund reaction
3102:Pinacol coupling reaction
3097:Piancatelli rearrangement
2992:LiebeskindâSrogl coupling
2842:FujimotoâBelleau reaction
2559:List of organic reactions
2423:Negative hyperconjugation
2168:
2110:
2001:10.1002/9783527651733.ch2
1922:10.1002/9783527639328.ch6
838:BuchwaldâHartwig reaction
751:BuchwaldâHartwig reaction
642:LiebeskindâSrogl coupling
5396:Organometallic chemistry
5327:PictetâSpengler reaction
5242:EinhornâBrunner reaction
5207:Boger pyridine synthesis
5101:Oxo-DielsâAlder reaction
5016:Aza-DielsâAlder reaction
4913:PictetâSpengler reaction
4813:HofmannâLöffler reaction
4803:Hegedus indole synthesis
4773:Fischer indole synthesis
4648:Bartoli indole synthesis
4603:Willgerodt rearrangement
4433:McLafferty rearrangement
4343:Ferrier carbocyclization
4158:2,3-Wittig rearrangement
4148:1,2-Wittig rearrangement
3988:ParikhâDoering oxidation
3978:Oxygen rebound mechanism
3643:AdkinsâPeterson reaction
3535:Yamaguchi esterification
3475:Hegedus indole synthesis
3440:Bartoli indole synthesis
3311:BamfordâStevens reaction
3227:Weinreb ketone synthesis
3187:Stork enamine alkylation
2962:Knoevenagel condensation
2832:Ferrier carbocyclization
2722:CastroâStephens coupling
2348:Hammett acidity function
2338:Free-energy relationship
2283:CurtinâHammett principle
2268:Conformational isomerism
962:Chemical Society Reviews
375:Cu-catalyzed version by
322:CastroâStephens coupling
89:Nobel Prize in Chemistry
5287:Knorr pyrrole synthesis
5222:BuchererâBergs reaction
5167:AllanâRobinson reaction
5146:Wagner-Jauregg reaction
4938:Ring-closing metathesis
4863:Larock indole synthesis
4843:Knorr pyrrole synthesis
4698:BuchererâBergs reaction
4563:Stieglitz rearrangement
4543:SkattebĂžl rearrangement
4513:Ring-closing metathesis
4373:Group transfer reaction
4338:Favorskii rearrangement
4278:Cornforth rearrangement
4208:Bamberger rearrangement
4113:WolffâKishner reduction
3933:MarkĂłâLam deoxygenation
3828:FlemingâTamao oxidation
3823:FischerâTropsch process
3510:Oxymercuration reaction
3490:Knorr pyrrole synthesis
3316:BartonâKellogg reaction
3222:Wagner-Jauregg reaction
3142:Ring-closing metathesis
3132:ReimerâTiemann reaction
3122:RauhutâCurrier reaction
3037:Nef isocyanide reaction
2997:Malonic ester synthesis
2967:Knorr pyrrole synthesis
2902:High dilution principle
2837:FriedelâCrafts reaction
2772:Cross-coupling reaction
2697:BuchererâBergs reaction
2682:Blanc chloromethylation
2672:Blaise ketone synthesis
2647:BaylisâHillman reaction
2642:BartonâKellogg reaction
2617:AllanâRobinson reaction
2523:WoodwardâHoffmann rules
2258:Charge-transfer complex
906:Miscellaneous reactions
203:Heterogeneous catalysts
107:Mechanism proposed for
36:cross-coupling reaction
5252:FeistâBenary synthesis
5026:Bradsher cycloaddition
4996:4+4 Photocycloaddition
4953:SimmonsâSmith reaction
4898:PaternĂČâBĂŒchi reaction
4758:FeistâBenary synthesis
4748:Dieckmann condensation
4498:Pummerer rearrangement
4478:Oxy-Cope rearrangement
4453:Myers allene synthesis
4403:Jacobsen rearrangement
4318:Electrocyclic reaction
4293:Demjanov rearrangement
4248:Buchner ring expansion
4218:Beckmann rearrangement
4198:Aza-Cope rearrangement
4193:ArndtâEistert reaction
4168:Alkyne zipper reaction
4088:Transfer hydrogenation
4063:Sharpless oxyamination
4038:Selenoxide elimination
3923:Lombardo methylenation
3848:Griesbaum coozonolysis
3758:CoreyâItsuno reduction
3733:BoylandâSims oxidation
3673:AngeliâRimini reaction
3321:Boord olefin synthesis
3265:ArndtâEistert reaction
3257:Homologation reactions
3057:Nitro-Mannich reaction
2972:KolbeâSchmitt reaction
2782:Cross-coupling partner
2702:Buchner ring expansion
2622:ArndtâEistert reaction
2388:Kinetic isotope effect
2135:Rearrangement reaction
1462:10.1002/anie.201107017
765:
189:
139:). This intermediate L
120:
87:were awarded the 2010
5111:PausonâKhand reaction
4948:Sharpless epoxidation
4903:Pechmann condensation
4783:FriedlÀnder synthesis
4733:DavisâBeirut reaction
4588:Wallach rearrangement
4558:Stevens rearrangement
4493:Pinacol rearrangement
4473:Overman rearrangement
4388:Hofmann rearrangement
4383:Hayashi rearrangement
4348:Ferrier rearrangement
4303:Dimroth rearrangement
4288:Curtius rearrangement
4283:Criegee rearrangement
4263:Claisen rearrangement
4253:Carroll rearrangement
4188:Amadori rearrangement
4178:Allylic rearrangement
4058:Sharpless epoxidation
3793:DessâMartin oxidation
3718:BohnâSchmidt reaction
3578:Hofmann rearrangement
3381:Kauffmann olefination
3304:Olefination reactions
3242:WurtzâFittig reaction
3077:PalladiumâNHC complex
2957:Kauffmann olefination
2912:Homologation reaction
2762:CoreyâHouse synthesis
2742:Claisen rearrangement
2538:YukawaâTsuno equation
2498:SwainâLupton equation
2478:Spherical aromaticity
2413:MöbiusâHĂŒckel concept
2198:Aromatic ring current
2160:Substitution reaction
1528:"Removing Impurities"
916:CâH functionalisation
807:Ullmann-type reaction
763:
739:ÎČ-hydride elimination
495:Stille cross coupling
349:CoreyâHouse synthesis
183:
169:reductive elimination
129:reductive elimination
106:
5317:PaalâKnorr synthesis
5187:BartonâZard reaction
5131:Staudinger synthesis
5081:Ketene cycloaddition
5051:DielsâAlder reaction
5031:Cheletropic reaction
5011:Alkyne trimerisation
4893:PaalâKnorr synthesis
4858:Kulinkovich reaction
4833:Jacobsen epoxidation
4753:DielsâAlder reaction
4548:Smiles rearrangement
4538:Sigmatropic reaction
4423:Lossen rearrangement
4273:CoreyâFuchs reaction
4238:Boekelheide reaction
4233:Bergmann degradation
4163:Achmatowicz reaction
3948:Methionine sulfoxide
3748:Clemmensen reduction
3708:Bergmann degradation
3638:Acyloin condensation
3603:Strecker degradation
3558:Bergmann degradation
3525:Ullmann condensation
3391:Peterson olefination
3366:Hydrazone iodination
3346:Elimination reaction
3247:ZinckeâSuhl reaction
3167:Sonogashira coupling
3127:Reformatsky reaction
3087:Peterson olefination
3052:Nierenstein reaction
2982:Kulinkovich reaction
2797:DielsâAlder reaction
2757:CoreyâFuchs reaction
2737:Claisen condensation
2607:Alkyne trimerisation
2582:Acyloin condensation
2548:ÎŁ-bishomoaromaticity
2508:ThorpeâIngold effect
2120:Elimination reaction
440:Sonogashira coupling
186:Sonogashira coupling
5337:Prilezhaev reaction
5322:Pellizzari reaction
5001:(4+3) cycloaddition
4968:Van Leusen reaction
4943:Robinson annulation
4928:Pschorr cyclization
4923:Prilezhaev reaction
4653:Bergman cyclization
4608:Wolff rearrangement
4593:Weerman degradation
4483:Pericyclic reaction
4463:Neber rearrangement
4358:Fries rearrangement
4243:Brook rearrangement
4228:Bergman cyclization
4073:Staudinger reaction
4018:Rosenmund reduction
4008:Reductive amination
3973:Oppenauer oxidation
3763:CoreyâKim oxidation
3738:Cannizzaro reaction
3613:Weerman degradation
3588:Isosaccharinic acid
3500:Mukaiyama hydration
3356:Hofmann elimination
3341:Dehydrohalogenation
3326:Chugaev elimination
3147:Robinson annulation
3092:Pfitzinger reaction
2862:Gattermann reaction
2807:WulffâDötz reaction
2787:DakinâWest reaction
2712:Carbonyl allylation
2657:Bergman cyclization
2443:Kennedy J. P. Orton
2363:Hammond's postulate
2333:FlippinâLodge angle
2303:Electromeric effect
2228:Beta-silicon effect
2213:BakerâNathan effect
1874:(19): 12564â12649.
1828:10.1021/jo01328a016
1783:Smith, Michael B.;
1129:10.1021/cr00039a007
127:generally involves
123:In such cases, the
67:carbonâcarbon bonds
5391:Coupling reactions
5086:McCormack reaction
5036:Conia-ene reaction
4868:Madelung synthesis
4658:Biginelli reaction
4448:Mumm rearrangement
4333:Favorskii reaction
4268:Cope rearrangement
4258:Chan rearrangement
4023:Rubottom oxidation
3953:Miyaura borylation
3918:Lipid peroxidation
3913:Lindgren oxidation
3893:Kornblum oxidation
3888:Kolbe electrolysis
3833:Fukuyama reduction
3743:Carbonyl reduction
3593:Marker degradation
3455:Diazonium compound
3445:Boudouard reaction
3424:Carbon-heteroatom
3351:Grieco elimination
3137:Rieche formylation
3082:Passerini reaction
3012:Meerwein arylation
2932:Hydroxymethylation
2827:Favorskii reaction
2727:Chan rearrangement
2662:Biginelli reaction
2587:Aldol condensation
2433:2-Norbornyl cation
2408:Möbius aromaticity
2403:Markovnikov's rule
2298:Effective molarity
2243:BĂŒrgiâDunitz angle
2233:Bicycloaromaticity
1995:. pp. 23â90.
974:10.1039/c1cs15088j
920:electron deficient
766:
556:Murahashi coupling
190:
149:oxidative addition
121:
71:coupling reactions
5378:
5377:
5374:
5373:
5370:
5369:
5362:WohlâAue reaction
5006:6+4 Cycloaddition
4823:Iodolactonization
4143:1,2-rearrangement
4108:WohlâAue reaction
4028:Sabatier reaction
3993:Pinnick oxidation
3958:Mozingo reduction
3903:Leuckart reaction
3858:Haloform reaction
3773:Criegee oxidation
3753:Collins oxidation
3703:Benkeser reaction
3698:Bechamp reduction
3668:Andrussow process
3653:Alcohol oxidation
3563:Edman degradation
3470:Haloform reaction
3419:
3418:
3406:Takai olefination
3371:Julia olefination
3197:Takai olefination
3072:Olefin metathesis
2947:Julia olefination
2872:Grignard reaction
2852:Fukuyama coupling
2767:Coupling reaction
2732:ChanâLam coupling
2602:Alkyne metathesis
2597:Alkane metathesis
2453:Phosphaethynolate
2358:George S. Hammond
2318:Electronic effect
2273:Conjugated system
2155:Stereospecificity
2150:Stereoselectivity
2115:Addition reaction
2104:organic reactions
2038:10.1021/jm200187y
2032:(10): 3451â3479.
1970:10.1021/ja062509l
1954:(27): 8754â8756.
1948:J. Am. Chem. Soc.
1850:Organic Chemistry
1822:(14): 2408â2417.
1800:978-0-471-72091-1
1752:10.1021/cr100259t
1713:10.1021/cr9000786
1643:10.1021/cr8002505
1608:10.1021/cr0505268
1565:10.1021/cr0505674
1505:10.1021/cr400274j
1499:(18): 9219â9280.
1456:(21): 5062â5085.
1413:978-3-540-01603-8
1380:978-1-84973-896-5
1351:10.1021/cr0505268
1300:(13): 8192â8228.
1253:(13): 9016â9085.
1230:10.1021/cr9000786
1185:(13): 8192â8228.
1150:10.1021/cr0509861
1144:(11): 4622â4643.
1083:10.1021/cr100355b
1044:10.1021/cr100327p
1003:10.1021/cr0505674
903:
902:
872:ChanâLam coupling
781:
780:
735:
734:
614:Fukuyama coupling
32:organic chemistry
16:(Redirected from
5413:
5357:Wenker synthesis
5347:Stollé synthesis
5202:Bobbitt reaction
5172:Auwers synthesis
5116:Povarov reaction
5041:Cyclopropanation
4979:
4973:Wenker synthesis
4728:Darzens reaction
4678:Bobbitt reaction
4523:Schmidt reaction
4328:Enyne metathesis
4103:Whiting reaction
4098:Wharton reaction
4043:Shapiro reaction
4033:Sarett oxidation
3998:Prévost reaction
3808:Emde degradation
3618:Wohl degradation
3598:Ruff degradation
3568:Emde degradation
3465:Grignard reagent
3401:Shapiro reaction
3386:McMurry reaction
3253:
3217:Ullmann reaction
3182:Stollé synthesis
3172:Stetter reaction
3162:Shapiro reaction
3152:Sakurai reaction
3047:Negishi coupling
3027:Minisci reaction
3022:Michael reaction
3007:McMurry reaction
3002:Mannich reaction
2882:Hammick reaction
2877:Grignard reagent
2817:Enyne metathesis
2802:Doebner reaction
2792:Darzens reaction
2637:Barbier reaction
2627:Auwers synthesis
2554:
2528:Woodward's rules
2493:Superaromaticity
2483:Spiroaromaticity
2383:Inductive effect
2378:Hyperconjugation
2353:Hammett equation
2293:Edwards equation
2145:Regioselectivity
2096:
2089:
2082:
2073:
2066:
2056:
2050:
2049:
2021:
2015:
2014:
1988:
1982:
1981:
1963:
1942:
1936:
1935:
1908:
1902:
1901:
1891:
1868:Chemical Reviews
1859:
1853:
1846:
1840:
1839:
1810:
1804:
1803:
1780:
1774:
1773:
1763:
1746:(3): 1346â1416.
1740:Chemical Reviews
1731:
1725:
1724:
1707:(3): 1435â1462.
1701:Chemical Reviews
1696:
1690:
1689:
1672:(5): 1485â1493.
1661:
1655:
1654:
1637:(8): 3054â3131.
1631:Chemical Reviews
1626:
1620:
1619:
1602:(7): 2651â2710.
1596:Chemical Reviews
1591:
1585:
1584:
1553:Chemical Reviews
1548:
1542:
1541:
1539:
1538:
1523:
1517:
1516:
1493:Chemical Reviews
1488:
1482:
1481:
1445:
1439:
1438:
1436:
1435:
1424:
1418:
1417:
1391:
1382:
1369:
1363:
1362:
1345:(7): 2651â2710.
1339:Chemical Reviews
1334:
1328:
1327:
1317:
1294:Chemical Reviews
1285:
1270:
1247:Chemical Reviews
1241:
1224:(3): 1435â1462.
1218:Chemical Reviews
1212:
1202:
1179:Chemical Reviews
1169:
1138:Chemical Reviews
1132:
1122:
1113:(7): 2457â2483.
1107:Chemical Reviews
1094:
1077:(3): 2251â2320.
1071:Chemical Reviews
1065:
1055:
1038:(3): 1417â1492.
1032:Chemical Reviews
1022:
991:Chemical Reviews
985:
783:
775:
756:
671:, gives ketones
468:Negishi coupling
270:
194:functional group
165:transmetallation
137:spectator ligand
52:
21:
5421:
5420:
5416:
5415:
5414:
5412:
5411:
5410:
5381:
5380:
5379:
5366:
5267:Gewald reaction
5150:
4977:
4958:Skraup reaction
4793:Graham reaction
4788:Gewald reaction
4619:
4612:
4134:
4127:
4083:Swern oxidation
4068:Stahl oxidation
4013:Riley oxidation
3968:Omega oxidation
3928:Luche reduction
3878:Jones oxidation
3843:Glycol cleavage
3838:Ganem oxidation
3783:Davis oxidation
3778:Dakin oxidation
3713:Birch reduction
3663:Amide reduction
3629:
3622:
3583:Hooker reaction
3545:
3539:
3427:
3425:
3415:
3411:Wittig reaction
3299:
3295:Wittig reaction
3270:Hooker reaction
3251:
3232:Wittig reaction
3207:Thorpe reaction
3192:Suzuki reaction
3177:Stille reaction
3112:Quelet reaction
2987:Kumada coupling
2937:Ivanov reaction
2927:Hydrovinylation
2907:Hiyama coupling
2867:Glaser coupling
2677:Blaise reaction
2667:Bingel reaction
2652:Benary reaction
2569:
2567:
2561:
2552:
2448:Passive binding
2368:Homoaromaticity
2218:Baldwin's rules
2193:Antiaromaticity
2188:Anomeric effect
2164:
2106:
2100:
2070:
2069:
2057:
2053:
2023:
2022:
2018:
2011:
1990:
1989:
1985:
1944:
1943:
1939:
1932:
1910:
1909:
1905:
1861:
1860:
1856:
1847:
1843:
1812:
1811:
1807:
1801:
1782:
1781:
1777:
1733:
1732:
1728:
1698:
1697:
1693:
1663:
1662:
1658:
1628:
1627:
1623:
1593:
1592:
1588:
1550:
1549:
1545:
1536:
1534:
1525:
1524:
1520:
1490:
1489:
1485:
1447:
1446:
1442:
1433:
1431:
1426:
1425:
1421:
1414:
1393:
1392:
1385:
1370:
1366:
1336:
1335:
1331:
1287:
1286:
1282:
1277:
1244:
1215:
1172:
1135:
1120:10.1.1.735.7660
1097:
1068:
1025:
988:
968:(10): 5151â69.
959:
956:
928:
908:
891:
882:
865:
848:
817:
773:
747:
715:
696:Cu, Fe, Pd etc.
658:RCO(SEt) Ar-SMe
652:
593:
583:Hiyama coupling
535:
525:Suzuki reaction
505:
385:Kumada coupling
359:
265:
217:
198:Organopalladium
178:
162:
158:
146:
142:
134:
109:Kumada coupling
97:
81:Ei-ichi Negishi
77:Richard F. Heck
50:
28:
23:
22:
15:
12:
11:
5:
5419:
5417:
5409:
5408:
5403:
5398:
5393:
5383:
5382:
5376:
5375:
5372:
5371:
5368:
5367:
5365:
5364:
5359:
5354:
5349:
5344:
5339:
5334:
5329:
5324:
5319:
5314:
5309:
5304:
5299:
5294:
5289:
5284:
5279:
5274:
5272:Hantzsch ester
5269:
5264:
5259:
5254:
5249:
5244:
5239:
5234:
5229:
5224:
5219:
5214:
5209:
5204:
5199:
5194:
5189:
5184:
5182:Banert cascade
5179:
5174:
5169:
5164:
5158:
5156:
5152:
5151:
5149:
5148:
5143:
5138:
5133:
5128:
5123:
5121:Prato reaction
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5083:
5078:
5073:
5068:
5063:
5058:
5053:
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5013:
5008:
5003:
4998:
4993:
4987:
4985:
4976:
4975:
4970:
4965:
4960:
4955:
4950:
4945:
4940:
4935:
4930:
4925:
4920:
4915:
4910:
4905:
4900:
4895:
4890:
4885:
4880:
4875:
4870:
4865:
4860:
4855:
4850:
4845:
4840:
4835:
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4750:
4745:
4740:
4735:
4730:
4725:
4720:
4715:
4710:
4705:
4700:
4695:
4690:
4685:
4680:
4675:
4670:
4665:
4660:
4655:
4650:
4645:
4640:
4635:
4630:
4624:
4622:
4614:
4613:
4611:
4610:
4605:
4600:
4595:
4590:
4585:
4580:
4575:
4570:
4565:
4560:
4555:
4550:
4545:
4540:
4535:
4530:
4525:
4520:
4515:
4510:
4505:
4500:
4495:
4490:
4485:
4480:
4475:
4470:
4465:
4460:
4455:
4450:
4445:
4440:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4375:
4370:
4365:
4360:
4355:
4350:
4345:
4340:
4335:
4330:
4325:
4320:
4315:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4213:Banert cascade
4210:
4205:
4200:
4195:
4190:
4185:
4180:
4175:
4170:
4165:
4160:
4155:
4150:
4145:
4139:
4137:
4133:Rearrangement
4129:
4128:
4126:
4125:
4123:Zinin reaction
4120:
4115:
4110:
4105:
4100:
4095:
4093:Wacker process
4090:
4085:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3985:
3980:
3975:
3970:
3965:
3960:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3890:
3885:
3880:
3875:
3870:
3868:Hydrogenolysis
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3818:Ătard reaction
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3723:Bosch reaction
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3634:
3632:
3628:Organic redox
3624:
3623:
3621:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3549:
3547:
3541:
3540:
3538:
3537:
3532:
3527:
3522:
3517:
3512:
3507:
3502:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3460:Esterification
3457:
3452:
3447:
3442:
3437:
3431:
3429:
3421:
3420:
3417:
3416:
3414:
3413:
3408:
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3368:
3363:
3358:
3353:
3348:
3343:
3338:
3333:
3328:
3323:
3318:
3313:
3307:
3305:
3301:
3300:
3298:
3297:
3292:
3287:
3282:
3277:
3272:
3267:
3261:
3259:
3250:
3249:
3244:
3239:
3237:Wurtz reaction
3234:
3229:
3224:
3219:
3214:
3209:
3204:
3199:
3194:
3189:
3184:
3179:
3174:
3169:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3109:
3107:Prins reaction
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2922:Hydrocyanation
2919:
2914:
2909:
2904:
2899:
2894:
2892:Henry reaction
2889:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2592:Aldol reaction
2589:
2584:
2579:
2573:
2571:
2566:Carbon-carbon
2563:
2562:
2557:
2551:
2550:
2545:
2543:Zaitsev's rule
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2488:Steric effects
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2169:
2166:
2165:
2163:
2162:
2157:
2152:
2147:
2142:
2140:Redox reaction
2137:
2132:
2127:
2125:Polymerization
2122:
2117:
2111:
2108:
2107:
2101:
2099:
2098:
2091:
2084:
2076:
2068:
2067:
2051:
2016:
2009:
1983:
1961:10.1.1.631.607
1937:
1930:
1903:
1854:
1841:
1805:
1799:
1775:
1726:
1691:
1666:Acc. Chem. Res
1656:
1621:
1586:
1559:(1): 133â173.
1543:
1518:
1483:
1440:
1419:
1412:
1404:10.1007/b94551
1383:
1364:
1329:
1279:
1278:
1276:
1273:
1272:
1271:
1242:
1213:
1170:
1133:
1099:Miyaura, Norio
1095:
1066:
1023:
997:(1): 133â173.
986:
955:
952:
927:
924:
907:
904:
901:
900:
898:
895:
892:
889:
886:
883:
880:
877:
874:
868:
867:
862:
859:
856:
853:
850:
846:
843:
840:
834:
833:
831:
828:
825:
822:
819:
815:
812:
809:
803:
802:
799:
796:
793:
790:
787:
779:
778:
769:
767:
746:
743:
733:
732:
729:
726:
723:
720:
717:
713:
710:
707:
701:
700:
697:
694:
691:
688:
685:
682:
679:
673:
672:
665:
662:
659:
656:
653:
650:
647:
644:
638:
637:
634:
631:
628:
625:
622:
619:
616:
610:
609:
608:requires base
606:
603:
600:
597:
594:
591:
588:
585:
579:
578:
576:
573:
570:
567:
564:
561:
558:
552:
551:
550:requires base
548:
545:
542:
539:
536:
533:
530:
527:
521:
520:
518:
515:
512:
509:
506:
503:
500:
497:
491:
490:
488:
485:
482:
479:
476:
473:
470:
464:
463:
462:requires base
460:
457:
454:
451:
448:
445:
442:
436:
435:
434:requires base
432:
429:
426:
423:
420:
417:
414:
408:
407:
405:
404:Pd or Ni or Fe
402:
399:
396:
393:
390:
387:
381:
380:
373:
370:
367:
364:
361:
357:
354:
351:
345:
344:
342:
339:
336:
333:
330:
327:
324:
318:
317:
316:requires base
314:
311:
308:
305:
302:
299:
296:
290:
289:
286:
283:
280:
277:
274:
264:
261:
255:, silicon, or
216:
215:Leaving groups
213:
177:
174:
160:
156:
153:organic halide
144:
140:
132:
131:of R-R' from L
96:
93:
63:
62:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5418:
5407:
5404:
5402:
5399:
5397:
5394:
5392:
5389:
5388:
5386:
5363:
5360:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5282:Herz reaction
5280:
5278:
5275:
5273:
5270:
5268:
5265:
5263:
5260:
5258:
5255:
5253:
5250:
5248:
5245:
5243:
5240:
5238:
5235:
5233:
5230:
5228:
5225:
5223:
5220:
5218:
5215:
5213:
5210:
5208:
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5178:
5175:
5173:
5170:
5168:
5165:
5163:
5160:
5159:
5157:
5153:
5147:
5144:
5142:
5139:
5137:
5134:
5132:
5129:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5089:
5087:
5084:
5082:
5079:
5077:
5074:
5072:
5069:
5067:
5064:
5062:
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5032:
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5012:
5009:
5007:
5004:
5002:
4999:
4997:
4994:
4992:
4989:
4988:
4986:
4984:
4983:Cycloaddition
4980:
4974:
4971:
4969:
4966:
4964:
4961:
4959:
4956:
4954:
4951:
4949:
4946:
4944:
4941:
4939:
4936:
4934:
4931:
4929:
4926:
4924:
4921:
4919:
4916:
4914:
4911:
4909:
4906:
4904:
4901:
4899:
4896:
4894:
4891:
4889:
4886:
4884:
4881:
4879:
4876:
4874:
4871:
4869:
4866:
4864:
4861:
4859:
4856:
4854:
4851:
4849:
4846:
4844:
4841:
4839:
4836:
4834:
4831:
4829:
4828:Isay reaction
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4739:
4736:
4734:
4731:
4729:
4726:
4724:
4723:Cycloaddition
4721:
4719:
4716:
4714:
4711:
4709:
4706:
4704:
4701:
4699:
4696:
4694:
4691:
4689:
4686:
4684:
4681:
4679:
4676:
4674:
4671:
4669:
4666:
4664:
4661:
4659:
4656:
4654:
4651:
4649:
4646:
4644:
4641:
4639:
4636:
4634:
4631:
4629:
4626:
4625:
4623:
4621:
4618:Ring forming
4615:
4609:
4606:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4579:
4576:
4574:
4571:
4569:
4566:
4564:
4561:
4559:
4556:
4554:
4551:
4549:
4546:
4544:
4541:
4539:
4536:
4534:
4531:
4529:
4526:
4524:
4521:
4519:
4518:Rupe reaction
4516:
4514:
4511:
4509:
4506:
4504:
4501:
4499:
4496:
4494:
4491:
4489:
4486:
4484:
4481:
4479:
4476:
4474:
4471:
4469:
4466:
4464:
4461:
4459:
4456:
4454:
4451:
4449:
4446:
4444:
4441:
4439:
4436:
4434:
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4376:
4374:
4371:
4369:
4366:
4364:
4361:
4359:
4356:
4354:
4351:
4349:
4346:
4344:
4341:
4339:
4336:
4334:
4331:
4329:
4326:
4324:
4321:
4319:
4316:
4314:
4311:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4140:
4138:
4136:
4130:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4019:
4016:
4014:
4011:
4009:
4006:
4004:
4001:
3999:
3996:
3994:
3991:
3989:
3986:
3984:
3981:
3979:
3976:
3974:
3971:
3969:
3966:
3964:
3961:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3908:Ley oxidation
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3873:Hydroxylation
3871:
3869:
3866:
3864:
3863:Hydrogenation
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3798:DNA oxidation
3796:
3794:
3791:
3789:
3788:Deoxygenation
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3678:Aromatization
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3635:
3633:
3631:
3625:
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:
3550:
3548:
3542:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3515:Reed reaction
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3432:
3430:
3426:bond forming
3422:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3372:
3369:
3367:
3364:
3362:
3359:
3357:
3354:
3352:
3349:
3347:
3344:
3342:
3339:
3337:
3334:
3332:
3331:Cope reaction
3329:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3308:
3306:
3302:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3262:
3260:
3258:
3254:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3042:Nef synthesis
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3017:Methylenation
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2887:Heck reaction
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2574:
2572:
2568:bond forming
2564:
2560:
2555:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2533:Y-aromaticity
2531:
2529:
2526:
2524:
2521:
2519:
2518:Walsh diagram
2516:
2514:
2511:
2509:
2506:
2504:
2503:Taft equation
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2473:ÎŁ-aromaticity
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2398:Marcus theory
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2373:HĂŒckel's rule
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2328:Evelyn effect
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2308:Electron-rich
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2223:Bema Hapothle
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2170:
2167:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2112:
2109:
2105:
2097:
2092:
2090:
2085:
2083:
2078:
2077:
2074:
2065:
2064:1-891389-53-X
2061:
2055:
2052:
2047:
2043:
2039:
2035:
2031:
2027:
2020:
2017:
2012:
2010:9783527328970
2006:
2002:
1998:
1994:
1987:
1984:
1979:
1975:
1971:
1967:
1962:
1957:
1953:
1950:
1949:
1941:
1938:
1933:
1931:9783527639328
1927:
1923:
1919:
1915:
1907:
1904:
1899:
1895:
1890:
1885:
1881:
1877:
1873:
1869:
1865:
1858:
1855:
1851:
1845:
1842:
1837:
1833:
1829:
1825:
1821:
1817:
1809:
1806:
1802:
1796:
1792:
1791:
1786:
1779:
1776:
1771:
1767:
1762:
1757:
1753:
1749:
1745:
1741:
1737:
1730:
1727:
1722:
1718:
1714:
1710:
1706:
1702:
1695:
1692:
1687:
1683:
1679:
1675:
1671:
1667:
1660:
1657:
1652:
1648:
1644:
1640:
1636:
1632:
1625:
1622:
1617:
1613:
1609:
1605:
1601:
1597:
1590:
1587:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1547:
1544:
1533:
1529:
1522:
1519:
1514:
1510:
1506:
1502:
1498:
1494:
1487:
1484:
1479:
1475:
1471:
1467:
1463:
1459:
1455:
1451:
1444:
1441:
1429:
1423:
1420:
1415:
1409:
1405:
1401:
1397:
1390:
1388:
1384:
1381:
1377:
1373:
1368:
1365:
1360:
1356:
1352:
1348:
1344:
1340:
1333:
1330:
1325:
1321:
1316:
1311:
1307:
1303:
1299:
1295:
1291:
1284:
1281:
1274:
1268:
1264:
1260:
1256:
1252:
1248:
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1214:
1210:
1206:
1201:
1196:
1192:
1188:
1184:
1180:
1176:
1171:
1167:
1163:
1159:
1155:
1151:
1147:
1143:
1139:
1134:
1130:
1126:
1121:
1116:
1112:
1108:
1104:
1103:Suzuki, Akira
1100:
1096:
1092:
1088:
1084:
1080:
1076:
1072:
1067:
1063:
1059:
1054:
1049:
1045:
1041:
1037:
1033:
1029:
1024:
1020:
1016:
1012:
1008:
1004:
1000:
996:
992:
987:
983:
979:
975:
971:
967:
963:
958:
957:
953:
951:
949:
945:
941:
937:
933:
925:
923:
921:
917:
913:
905:
899:
896:
893:
887:
884:
878:
875:
873:
870:
869:
864:N-C coupling,
863:
860:
857:
854:
851:
844:
841:
839:
836:
835:
832:
829:
826:
823:
820:
813:
810:
808:
805:
804:
800:
797:
788:
785:
784:
777:
770:
768:
762:
758:
757:
754:
752:
744:
742:
740:
730:
727:
724:
721:
718:
711:
708:
706:
703:
702:
698:
695:
692:
689:
686:
683:
680:
678:
675:
674:
670:
666:
663:
660:
657:
654:
648:
645:
643:
640:
639:
635:
632:
629:
626:
623:
620:
617:
615:
612:
611:
607:
604:
601:
598:
595:
589:
586:
584:
581:
580:
577:
574:
571:
568:
565:
562:
559:
557:
554:
553:
549:
546:
543:
540:
537:
531:
528:
526:
523:
522:
519:
516:
513:
510:
507:
501:
498:
496:
493:
492:
489:
486:
483:
480:
477:
474:
471:
469:
466:
465:
461:
458:
455:
452:
449:
446:
443:
441:
438:
437:
433:
430:
427:
424:
421:
418:
415:
413:
412:Heck reaction
410:
409:
406:
403:
400:
397:
394:
391:
388:
386:
383:
382:
378:
374:
371:
368:
365:
362:
355:
352:
350:
347:
346:
343:
340:
337:
334:
331:
328:
325:
323:
320:
319:
315:
312:
309:
306:
303:
300:
297:
295:
292:
291:
287:
284:
275:
272:
271:
268:
262:
260:
258:
254:
250:
246:
242:
238:
237:pseudohalides
234:
230:
226:
222:
221:leaving group
214:
212:
209:
206:
204:
199:
195:
187:
182:
175:
173:
170:
166:
154:
150:
138:
130:
126:
118:
114:
110:
105:
101:
94:
92:
90:
86:
82:
78:
74:
72:
68:
60:
56:
49:
48:
47:
45:
41:
37:
33:
19:
4323:Ene reaction
3683:Autoxidation
3544:Degradation
3435:Azo coupling
3212:Ugi reaction
2812:Ene reaction
2771:
2612:Alkynylation
2463:Polyfluorene
2458:Polar effect
2323:Electrophile
2238:Bredt's rule
2208:Baird's rule
2178:Alpha effect
2054:
2029:
2025:
2019:
1992:
1986:
1951:
1946:
1940:
1913:
1906:
1871:
1867:
1857:
1849:
1844:
1819:
1815:
1808:
1789:
1785:March, Jerry
1778:
1743:
1739:
1729:
1704:
1700:
1694:
1669:
1665:
1659:
1634:
1630:
1624:
1599:
1595:
1589:
1556:
1552:
1546:
1535:. Retrieved
1531:
1521:
1496:
1492:
1486:
1453:
1449:
1443:
1432:. Retrieved
1422:
1395:
1371:
1367:
1342:
1338:
1332:
1297:
1293:
1283:
1250:
1246:
1221:
1217:
1182:
1178:
1141:
1137:
1110:
1106:
1074:
1070:
1035:
1031:
994:
990:
965:
961:
929:
926:Applications
912:aryl halides
909:
814:ArO-MM, ArNH
771:
748:
736:
360:CuLi or RMgX
266:
218:
210:
207:
191:
135:MR(R') (L =
122:
98:
85:Akira Suzuki
75:
64:
35:
29:
2822:Ethenolysis
2468:Ring strain
2438:Nucleophile
2263:Clar's rule
2203:Aromaticity
948:resveratrol
944:varenicline
932:montelukast
792:Reactant A
279:Reactant A
227:, although
196:tolerance.
5385:Categories
5106:Ozonolysis
4633:Annulation
3983:Ozonolysis
2102:Topics in
1537:2015-12-11
1434:2010-10-06
1275:References
936:eletriptan
818:,RS-M,NC-M
795:Reactant B
693:sp, sp, sp
687:sp, sp, sp
508:sp, sp, sp
478:sp, sp, sp
282:Reactant B
201:product.
5406:Catalysis
4620:reactions
4135:reactions
3630:reactions
3546:reactions
3428:reactions
2570:reactions
1956:CiteSeerX
1836:0022-3263
1115:CiteSeerX
667:requires
575:Pd or Ru
459:Pd and Cu
176:Catalysts
159:M gives L
155:(RX) to L
125:mechanism
95:Mechanism
44:catalysts
18:Arylation
2513:Vinylogy
2183:Annulene
2130:Reagents
2046:21504168
1978:16819868
1898:27689804
1787:(2007),
1770:21133429
1721:20148539
1686:25916260
1651:18698737
1616:16836296
1581:36974481
1573:17212474
1513:25184859
1478:20582425
1470:22573393
1359:16836296
1324:31184483
1267:28639787
1238:20148539
1209:31184483
1158:17091930
1091:21391571
1062:21319862
1019:36974481
1011:17212474
982:21731956
940:naproxen
879:Ar-B(OR)
798:Catalyst
786:Reaction
633:Pd or Ni
627:RCO(SEt)
547:Pd or Ni
517:Pd or Ni
487:Pd or Ni
431:Pd or Ni
285:Catalyst
273:Reaction
233:tosylate
229:triflate
40:reaction
2173:A value
1889:5070552
1761:3055945
1315:6620169
1200:6620169
1166:8128630
1053:3075866
954:Reviews
922:arene.
801:Remark
649:R-B(OR)
566:sp, sp
532:R-B(OR)
379:, 1971
369:sp, sp
288:Remark
241:bromide
147:M. The
115:, Ar =
2062:
2044:
2007:
1976:
1958:
1928:
1896:
1886:
1834:
1797:
1768:
1758:
1719:
1684:
1649:
1614:
1579:
1571:
1511:
1476:
1468:
1410:
1378:
1357:
1322:
1312:
1265:
1236:
1207:
1197:
1164:
1156:
1117:
1089:
1060:
1050:
1017:
1009:
980:
946:, and
918:at an
728:Cu, Pd
725:sp, sp
655:sp, sp
621:R-Zn-I
475:R-Zn-X
447:ArCâĄCH
419:alkene
395:sp, sp
245:iodide
225:halide
151:of an
113:Ligand
83:, and
59:halide
1577:S2CID
1474:S2CID
1162:S2CID
1015:S2CID
888:Ar-NH
811:1905
789:Year
709:2000s
602:sp sp
590:R-SiR
563:R-Li
560:1979
544:sp sp
514:sp sp
502:R-SnR
484:sp sp
456:sp sp
392:RMgBr
377:Kochi
329:RCâĄCH
307:RCâĄCX
301:RCâĄCH
276:Year
257:boron
111:(L =
38:is a
2060:ISBN
2042:PMID
2005:ISBN
1974:PMID
1926:ISBN
1894:PMID
1832:ISSN
1795:ISBN
1766:PMID
1717:PMID
1682:PMID
1647:PMID
1612:PMID
1569:PMID
1509:PMID
1466:PMID
1408:ISBN
1376:ISBN
1355:PMID
1320:PMID
1263:PMID
1234:PMID
1205:PMID
1154:PMID
1087:PMID
1058:PMID
1007:PMID
978:PMID
876:1998
842:1994
774:Eq.1
722:R'-X
712:R-CO
690:R'-H
681:2004
669:CuTC
646:2000
618:1998
587:1988
569:R-X
529:1979
499:1978
472:1977
444:1975
425:Ar-X
416:1972
389:1972
353:1967
335:Ar-X
326:1963
298:1957
253:zinc
219:The
117:Aryl
55:aryl
34:, a
2034:doi
1997:doi
1966:doi
1952:128
1918:doi
1884:PMC
1876:doi
1872:116
1824:doi
1756:PMC
1748:doi
1744:111
1709:doi
1705:110
1674:doi
1639:doi
1635:108
1604:doi
1600:106
1561:doi
1557:107
1501:doi
1497:114
1458:doi
1400:doi
1347:doi
1343:106
1310:PMC
1302:doi
1298:119
1255:doi
1251:117
1226:doi
1222:110
1195:PMC
1187:doi
1183:119
1146:doi
1142:106
1125:doi
1079:doi
1075:111
1048:PMC
1040:doi
1036:111
999:doi
995:107
970:doi
855:R-X
849:N-H
684:R-H
599:R-X
572:sp
541:R-X
511:R-X
481:R-X
453:R-X
398:R-X
372:Cu
366:R-X
363:sp
249:tin
243:or
30:In
5387::
2040:.
2030:54
2028:.
2003:.
1972:.
1964:.
1924:.
1892:.
1882:.
1870:.
1866:.
1830:.
1820:44
1818:.
1764:.
1754:.
1742:.
1738:.
1715:.
1703:.
1680:.
1670:48
1668:.
1645:.
1633:.
1610:.
1598:.
1575:.
1567:.
1555:.
1530:.
1507:.
1495:.
1472:.
1464:.
1454:51
1452:.
1406:.
1386:^
1353:.
1341:.
1318:.
1308:.
1296:.
1292:.
1261:.
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