209:; X = Cl is marginal) will undergo coupling as the nucleophilic and electrophilic coupling partners, respectively. The reaction usually takes place at room temperature or below in an ethereal solvent. Due to the wide range of applicable coupling partners, functional group tolerance, and operational simplicity, the Corey–House synthesis is a powerful and practical tool for the synthesis of complex organic molecules. However, as limitations, hindered (2° or 3°) alkyl halides are generally unsuccessful or low-yielding substrates for the Corey-House synthesis. Furthermore, alkynylcuprates are generally inert under usual coupling conditions. The forging of aryl-aryl bonds is also inefficient and much more effectively achieved using
336:
304:
311:
be used successfully.) On the other hand, sterically hindered organocopper reagents, including 3° and other branched alkyl reagents, are generally tolerated. However, aryl bromides, iodides and sulfonates, which do not ordinarily undergo nucleophilic substitution in the absence of a transition metal, can be used successfully as coupling partners.
291:
When R and R' are different, only the cross product R–R' is obtained; R–R or R'–R' are not formed in significant amounts. The Corey–House reaction is therefore an example of a cross-coupling reaction. The Corey–House synthesis is, in fact, one of the earliest transition metal-mediated (or catalyzed,
310:
For this reaction to work successfully, the alkyl (pseudo)halide coupling partner should be methyl, benzylic, allylic, 1° alkyl, or 2° cycloalkyl. In most cases, 3° and acyclic 2° electrophiles give unsatisfactory results. (However, see below for recent modifications that allow 2° electrophiles to
346:
as the ligand for copper and lithium methoxide as a base additive, it is now possible to couple 1°, 2°, and 3° Grignard reagents with 1° and 2° alkyl bromides and tosylates in high yields with nearly exclusive stereoinversion. Even β-branched 2° alkyl tosylates react to give coupling product in
275:
From the stoichiometry, it is apparent that one equivalent of the R group is wasted as an ill-characterized alkylcopper species (likely polymeric; usually converted to RH upon aqueous workup) in the most common form of the Corey–House synthesis. To avoid this for cases where R is a precious or
299:
2-like mechanism to give a copper(III) species, which undergoes reductive elimination to give the coupling product. When alkyl iodides are used, scrambling of configuration is observed, and cyclization products are observed to form for alkyl iodides with an olefin tether, both of which are
327:
and alkyl bromides could be coupled using a catalytic amount of lithium tetrachlorocuprate(II), a process that was extended to alkyl tosylates by
Schlosser and Fouquet. In the catalytic process, the Grignard reagent undergoes transmetalation with the copper salt or complex to generate an
266:
The Corey-House synthesis process is the reaction between the organocopper reagent, usually a lithium dialkylcuprate as prepared above, and a second alkyl (pseudo)halide or an aryl iodide. This results in the formation of a C–C bond between the two organic fragments:
164:
and/or the formation of large amounts of reduction or elimination side-products. As a solution to this problem, the Corey–House reaction constitutes a general and high yielding method for the joining of two alkyl groups or an alkyl group and an aryl group.
159:
can react directly (without copper) with an alkyl halide in a nucleophilic substitution reaction to form a new carbon–carbon bond. However, aside from the use of metal acetylides as nucleophiles, such a process rarely works well in practice due to
712:
Yang, Chu-Ting; Zhang, Zhen-Qi; Liang, Jun; Liu, Jing-Hui; Lu, Xiao-Yu; Chen, Huan-Huan; Liu, Lei (2012-07-11). "Copper-Catalyzed Cross-Coupling of
Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents".
598:
In a typical example, lithium dibutylcuprate reacts with 2-bromopentane to give the coupling product in only 12% yield. However, aryl derived cuprate reagents can react successfully. For instance, lithium diphenylcuprate reacts with
355:
While the coupling of organocopper compounds and allyl bromide was reported as early as 1936 by Henry Gilman (Iowa State
University), this reaction was fully developed by four organic chemists (two at Harvard and two at MIT):
262:
If the use of alkyllithium reagents is precluded by functional group incompatibility, transmetalation from other metals (e.g., Mg, Zn, Al, B) may be considered as alternatives for the preparation of the organocopper reagent.
221:
The Corey-House synthesis is preceded by two preliminary steps to prepare the requisite Gilman reagent from an alkyl halide. In the first step, the alkyl halide is treated with lithium metal in dry ether to prepare an
3962:
492:
House, Herbert O.; Respess, William L.; Whitesides, George M. (1 October 1966). "The
Chemistry of Carbanions. XII. The Role of Copper in the Conjugate Addition of Organometallic Reagents".
564:
Whitesides, George M.; Fischer, William F.; San
Filippo, Joseph; Bashe, Robert W.; House, Herbert O. (1969-08-01). "Reaction of lithium dialkyl- and diarylcuprates with organic halides".
295:
In the case of alkyl bromides and tosylates, inversion of configuration is observed when an configurationally pure alkyl electrophile is used. The reaction is believed to proceed via an S
328:
organocuprate as a catalytic intermediate, which then undergoes reaction with the (pseudo)halide electrophile to form the coupling product and release the copper and complete the
125:
82:
3078:
3023:
3791:
3133:
3283:
1917:
4106:
4012:
3786:
2888:
1612:
2658:
809:
3458:
1402:
3553:
1657:
3533:
3028:
2195:
2076:
1632:
3623:
3378:
845:
2210:
465:
Corey, Elias J.; Posner, Gary H. (19 July 1967). "Selective formation of carbon-carbon bonds between unlike groups using organocopper reagents".
3856:
3313:
3806:
3418:
3398:
3358:
2165:
3952:
3877:
3761:
2373:
1777:
1108:
661:
384:
3947:
3776:
3433:
3288:
2918:
226:
reagent, RLi. The starting alkyl halide for the lithiation step can be a primary, secondary or tertiary alkyl chloride, bromide, or iodide:
2763:
2000:
3123:
2613:
2288:
4027:
3811:
2833:
3388:
4022:
3736:
3598:
3353:
545:
449:
3912:
3383:
3298:
3268:
3248:
3113:
3108:
2483:
2408:
2051:
2005:
1872:
1133:
3851:
4017:
3977:
3927:
3403:
3153:
3083:
1572:
3613:
3218:
2111:
1832:
3603:
1143:
3771:
3528:
3478:
2268:
2200:
2091:
1667:
1422:
1347:
1128:
3483:
3293:
2768:
2678:
802:
394:
4057:
3841:
3781:
3183:
3158:
3068:
2648:
2528:
1562:
1058:
3942:
3428:
3223:
1492:
4047:
3633:
3143:
2653:
2598:
2443:
2403:
2235:
1990:
1707:
1557:
4007:
3568:
3523:
3013:
2868:
4042:
3957:
3816:
3731:
3628:
2703:
2358:
2026:
1437:
998:
3932:
3907:
3892:
3588:
3453:
3408:
3173:
2718:
2568:
1782:
1462:
1407:
3937:
3882:
3413:
2828:
2543:
2538:
2031:
1847:
1837:
1552:
1412:
1362:
1357:
1332:
1238:
756:
Gilman, Henry; Straley, James M. (2010). "Relative reactivities of organometallic compounds. XIII. Copper and silver".
3992:
3593:
3513:
3128:
3093:
2938:
2363:
2323:
2220:
1995:
1747:
1692:
1292:
1003:
993:
968:
3967:
3668:
3473:
2908:
2473:
2448:
2388:
1980:
1687:
1337:
1522:
3258:
2793:
2245:
1467:
1432:
1028:
963:
795:
343:
3826:
3448:
2508:
2433:
1957:
1792:
1253:
1213:
958:
4067:
3972:
3706:
3678:
3648:
3563:
3493:
3423:
3343:
3243:
3203:
2898:
2518:
1817:
1812:
1274:
1138:
677:
Fouquet, Gerd; Schlosser, Manfred (1974-01-01). "Improved Carbon-Carbon
Linking by Controlled Copper Catalysis".
347:
moderate yield, greatly expanding the scope of the catalytic Corey–House synthesis (Kochi–Schlosser coupling).
4032:
3902:
3766:
3608:
3468:
2988:
1962:
1512:
1472:
1223:
3922:
3518:
3488:
3363:
3318:
3148:
3058:
2873:
2863:
2693:
2250:
2190:
2155:
1942:
1902:
1677:
1547:
1063:
1053:
983:
374:
3498:
2478:
1502:
1048:
928:
3711:
4111:
4002:
3861:
3653:
3578:
3558:
3278:
3228:
3088:
3053:
2993:
2923:
2225:
2205:
1937:
1857:
1752:
1712:
1682:
1617:
1487:
1397:
1387:
1263:
973:
173:
The scope of the Corey-House synthesis is exceptionally broad, and a range of lithium diorganylcuprates (R
3741:
3463:
3213:
3193:
3168:
3118:
3033:
3008:
2963:
2933:
2913:
2883:
2848:
2803:
2778:
2753:
2638:
2563:
2343:
2036:
1972:
1772:
1497:
1417:
1103:
1078:
855:
850:
4077:
2823:
1447:
3663:
3618:
3333:
3303:
3273:
3208:
3188:
3103:
3098:
3063:
3018:
3003:
2998:
2978:
2968:
2903:
2893:
2773:
2293:
2096:
1672:
1627:
1457:
1193:
913:
875:
243:
223:
161:
152:
132:
1123:
1118:
3716:
52:
17:
3846:
3796:
3746:
3726:
3573:
3548:
3263:
3253:
3138:
2953:
2948:
2878:
2663:
2463:
2423:
2353:
2318:
2273:
2240:
2106:
2081:
2061:
1882:
1842:
1802:
1767:
1697:
1452:
1322:
1297:
835:
380:
4062:
4052:
4037:
3683:
3658:
3643:
3638:
3368:
3323:
3308:
3198:
3178:
3073:
2958:
2943:
2788:
2733:
2723:
2713:
2688:
2453:
2328:
2303:
2215:
2071:
2056:
2041:
1897:
1862:
1807:
1577:
1427:
1372:
1243:
1158:
1018:
943:
1088:
3801:
3751:
3721:
3583:
3373:
3163:
3048:
2983:
2973:
2738:
2668:
2633:
2628:
2608:
2603:
2548:
2458:
2308:
2170:
2160:
2066:
1852:
1797:
1727:
1647:
1542:
1442:
1377:
1302:
1148:
1013:
948:
364:
95:
933:
3538:
2858:
2743:
2708:
2673:
2618:
2573:
2533:
2488:
2468:
2418:
2413:
2383:
2368:
2278:
2185:
2121:
2086:
1912:
1787:
1662:
1587:
1567:
1482:
1317:
1312:
1258:
1168:
1073:
1033:
988:
870:
865:
830:
773:
738:
730:
694:
657:
634:
581:
541:
445:
324:
4072:
3917:
3887:
3831:
3756:
3688:
3443:
3393:
3238:
3043:
2818:
2813:
2758:
2748:
2523:
2333:
2313:
2283:
2180:
2116:
2101:
1932:
1887:
1877:
1867:
1762:
1742:
1737:
1722:
1717:
1597:
1592:
1532:
1517:
1507:
1352:
1342:
1208:
1198:
1188:
1098:
1093:
1068:
1008:
860:
819:
765:
722:
686:
626:
573:
501:
474:
437:
390:
251:
156:
39:
3982:
3673:
3508:
3503:
2798:
2783:
2728:
2683:
2643:
2593:
2558:
2553:
2498:
2493:
2428:
2378:
2298:
2126:
2010:
1985:
1947:
1922:
1907:
1892:
1827:
1702:
1652:
1642:
1622:
1582:
1392:
1382:
1367:
1163:
1083:
908:
903:
617:
TAMURA, M.; KOCHI, J. (1971-01-01). "Coupling of
Grignard Reagents with Organic Halides".
335:
329:
210:
953:
923:
3987:
3897:
3836:
2928:
2838:
2808:
2583:
2438:
2175:
1952:
1822:
1637:
1607:
1307:
1203:
978:
840:
519:
412:
407:
370:
235:
4100:
3997:
3698:
3543:
3438:
3233:
2623:
2588:
2578:
2513:
2503:
2393:
2230:
2046:
1757:
1732:
1602:
1248:
1233:
1218:
1113:
1043:
1023:
938:
247:
3038:
2398:
2150:
1927:
1527:
1327:
1178:
1173:
1038:
893:
239:
89:
1537:
1183:
1153:
918:
441:
3821:
3348:
2698:
787:
360:
85:
777:
769:
734:
698:
638:
585:
432:
Posner, G. H. (1975). "Substitution
Reactions using Organo Copper Reagents".
320:
742:
690:
1228:
898:
630:
206:
202:
194:
577:
505:
478:
303:
888:
198:
186:
46:
43:
726:
607:)-2-phenylbutane (67-68% ee) in 67-87% yield (84-92% stereoinversion).
288:= cyano, alkynyl, 2-thienyl, etc.) can be prepared and used instead.
190:
128:
178:
182:
1272:
791:
387:; later Harvard University), junior colleague of Herbert House
334:
302:
526:
generated organosodium reagent reacts with an alkyl halide.
201:, 1°, or cyclic 2° alkyl, aryl, or alkenyl and X = Br, I,
67:
292:
see below) cross-coupling reactions to be discovered.
536:
Lipshutz, Bruce H. (2002). Schlosser, Manfred (ed.).
98:
55:
3963:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
3870:
3697:
3332:
2847:
2342:
2259:
2139:
2019:
1971:
1281:
135:species and lithium (pseudo)halide as byproducts.
679:Angewandte Chemie International Edition in English
119:
76:
3024:Divinylcyclopropane-cycloheptadiene rearrangement
151:In principle, a carbanion equivalent such as an
3284:Thermal rearrangement of aromatic hydrocarbons
1918:Thermal rearrangement of aromatic hydrocarbons
656:. New York: Academic Press. pp. 381–386.
393:(Massachusetts Institute of Technology; later
377:), a student of Harvard University at the time
238:, also known as a Gilman reagent (named after
4013:Lectka enantioselective beta-lactam synthesis
803:
8:
3792:Inverse electron-demand Diels–Alder reaction
1613:Heterogeneous metal catalyzed cross-coupling
342:Under recently discovered conditions, using
3134:Lobry de Bruyn–Van Ekenstein transformation
300:indicative of the involvement of radicals.
3694:
1968:
1269:
810:
796:
788:
758:Recueil des Travaux Chimiques des Pays-Bas
284:is an untransferable dummy ligand (e.g., R
3624:Petrenko-Kritschenko piperidone synthesis
3079:Fritsch–Buttenberg–Wiechell rearrangement
108:
99:
97:
66:
61:
56:
54:
3787:Intramolecular Diels–Alder cycloaddition
715:Journal of the American Chemical Society
566:Journal of the American Chemical Society
467:Journal of the American Chemical Society
654:Organometallic Mechanisms and Catalysis
603:)-2-bromobutane (73-78% ee) to afford (
424:
189:) and organyl (pseudo)halides (RX, R =
3807:Metal-centered cycloaddition reactions
3459:Debus–Radziszewski imidazole synthesis
1403:Bodroux–Chichibabin aldehyde synthesis
538:Organometallics in Synthesis: A Manual
36:Corey–Posner–Whitesides–House reaction
18:Corey–House–Posner–Whitesides reaction
3953:Diazoalkane 1,3-dipolar cycloaddition
3857:Vinylcyclopropane (5+2) cycloaddition
3762:Diazoalkane 1,3-dipolar cycloaddition
3534:Hurd–Mori 1,2,3-thiadiazole synthesis
3029:Dowd–Beckwith ring-expansion reaction
2196:Hurd–Mori 1,2,3-thiadiazole synthesis
1109:LFER solvent coefficients (data page)
385:Massachusetts Institute of Technology
254:(CuI) in a transmetalation reaction:
7:
4107:Carbon-carbon bond forming reactions
2764:Sharpless asymmetric dihydroxylation
2001:Methoxymethylenetriphenylphosphorane
559:
557:
2889:Allen–Millar–Trippett rearrangement
4028:Nitrone-olefin (3+2) cycloaddition
4023:Niementowski quinazoline synthesis
3812:Nitrone-olefin (3+2) cycloaddition
3737:Azide-alkyne Huisgen cycloaddition
3599:Niementowski quinazoline synthesis
3354:Azide-alkyne Huisgen cycloaddition
2659:Meerwein–Ponndorf–Verley reduction
2211:Leimgruber–Batcho indole synthesis
436:. Vol. 22. pp. 253–400.
367:), research advisor of Gary Posner
25:
3852:Trimethylenemethane cycloaddition
3554:Johnson–Corey–Chaykovsky reaction
3419:Cadogan–Sundberg indole synthesis
3399:Bohlmann–Rahtz pyridine synthesis
3359:Baeyer–Emmerling indole synthesis
2166:Cadogan–Sundberg indole synthesis
1658:Johnson–Corey–Chaykovsky reaction
276:complex fragment, a reagent (R)(R
77:{\displaystyle {\ce {R_{2}CuLi}}}
3948:Cook–Heilbron thiazole synthesis
3777:Hexadehydro Diels–Alder reaction
3604:Niementowski quinoline synthesis
3434:Cook–Heilbron thiazole synthesis
3379:Bischler–Möhlau indole synthesis
3289:Tiffeneau–Demjanov rearrangement
2919:Baker–Venkataraman rearrangement
2077:Horner–Wadsworth–Emmons reaction
1748:Mizoroki-Heck vs. Reductive Heck
1633:Horner–Wadsworth–Emmons reaction
1144:Neighbouring group participation
494:The Journal of Organic Chemistry
42:that involves the reaction of a
3484:Fiesselmann thiophene synthesis
3314:Westphalen–Lettré rearrangement
3294:Vinylcyclopropane rearrangement
3124:Kornblum–DeLaMare rearrangement
2769:Epoxidation of allylic alcohols
2679:Noyori asymmetric hydrogenation
2614:Kornblum–DeLaMare rearrangement
2289:Gallagher–Hollander degradation
395:Georgia Institute of Technology
3943:Chichibabin pyridine synthesis
3429:Chichibabin pyridine synthesis
3389:Blum–Ittah aziridine synthesis
3224:Ring expansion and contraction
1493:Cross dehydrogenative coupling
271:Li + R'–X → R–R' + "RCu" + LiX
217:Reaction process and mechanism
38:and other permutations) is an
1:
3913:Bischler–Napieralski reaction
3871:Heterocycle forming reactions
3524:Hemetsberger indole synthesis
3384:Bischler–Napieralski reaction
3299:Wagner–Meerwein rearrangement
3269:Sommelet–Hauser rearrangement
3249:Seyferth–Gilbert homologation
3114:Ireland–Claisen rearrangement
3109:Hofmann–Martius rearrangement
2869:2,3-sigmatropic rearrangement
2484:Corey–Winter olefin synthesis
2409:Barton–McCombie deoxygenation
2052:Corey–Winter olefin synthesis
2006:Seyferth–Gilbert homologation
1873:Seyferth–Gilbert homologation
4018:Lehmstedt–Tanasescu reaction
3978:Gabriel–Colman rearrangement
3933:Bucherer carbazole synthesis
3928:Borsche–Drechsel cyclization
3908:Bernthsen acridine synthesis
3893:Bamberger triazine synthesis
3878:Algar–Flynn–Oyamada reaction
3589:Nazarov cyclization reaction
3454:De Kimpe aziridine synthesis
3409:Bucherer carbazole synthesis
3404:Borsche–Drechsel cyclization
3174:Nazarov cyclization reaction
3154:Meyer–Schuster rearrangement
3084:Gabriel–Colman rearrangement
2834:Wolffenstein–Böters reaction
2719:Reduction of nitro compounds
2569:Grundmann aldehyde synthesis
2374:Algar–Flynn–Oyamada reaction
1783:Olefin conversion technology
1778:Nozaki–Hiyama–Kishi reaction
1573:Gabriel–Colman rearrangement
1463:Claisen-Schmidt condensation
1408:Bouveault aldehyde synthesis
131:, as well as an ill-defined
120:{\displaystyle {\ce {R'-X}}}
3993:Hantzsch pyridine synthesis
3772:Enone–alkene cycloadditions
3594:Nenitzescu indole synthesis
3514:Hantzsch pyridine synthesis
3479:Ferrario–Ackermann reaction
3129:Kowalski ester homologation
3094:Halogen dance rearrangement
2939:Benzilic acid rearrangement
2364:Akabori amino-acid reaction
2324:Von Braun amide degradation
2269:Barbier–Wieland degradation
2221:Nenitzescu indole synthesis
2201:Kharasch–Sosnovsky reaction
2092:Julia–Kocienski olefination
1996:Kowalski ester homologation
1693:Kowalski ester homologation
1668:Julia–Kocienski olefination
1423:Cadiot–Chodkiewicz coupling
1348:Aza-Baylis–Hillman reaction
1293:Acetoacetic ester synthesis
1004:Dynamic binding (chemistry)
994:Conrotatory and disrotatory
969:Charge remote fragmentation
540:. Wiley. pp. 665–815.
442:10.1002/0471264180.or022.02
4128:
4058:Robinson–Gabriel synthesis
4008:Kröhnke pyridine synthesis
3842:Retro-Diels–Alder reaction
3782:Imine Diels–Alder reaction
3569:Kröhnke pyridine synthesis
3184:Newman–Kwart rearrangement
3159:Mislow–Evans rearrangement
3069:Fischer–Hepp rearrangement
3014:Di-π-methane rearrangement
2794:Stephen aldehyde synthesis
2529:Eschweiler–Clarke reaction
2246:Williamson ether synthesis
1563:Fujiwara–Moritani reaction
1468:Combes quinoline synthesis
1433:Carbonyl olefin metathesis
1134:More O'Ferrall–Jencks plot
1059:Grunwald–Winstein equation
1029:Electron-withdrawing group
964:Catalytic resonance theory
4068:Urech hydantoin synthesis
4048:Pomeranz–Fritsch reaction
3973:Fischer oxazole synthesis
3707:1,3-Dipolar cycloaddition
3679:Urech hydantoin synthesis
3649:Reissert indole synthesis
3634:Pomeranz–Fritsch reaction
3564:Knorr quinoline synthesis
3494:Fischer oxazole synthesis
3424:Camps quinoline synthesis
3344:1,3-Dipolar cycloaddition
3244:Semipinacol rearrangement
3219:Ramberg–Bäcklund reaction
3204:Piancatelli rearrangement
3144:McFadyen–Stevens reaction
2899:Alpha-ketol rearrangement
2654:McFadyen–Stevens reaction
2599:Kiliani–Fischer synthesis
2519:Elbs persulfate oxidation
2444:Bouveault–Blanc reduction
2404:Baeyer–Villiger oxidation
2236:Schotten–Baumann reaction
2112:Ramberg–Bäcklund reaction
1991:Kiliani–Fischer synthesis
1833:Ramberg–Bäcklund reaction
1818:Pinacol coupling reaction
1813:Piancatelli rearrangement
1708:Liebeskind–Srogl coupling
1558:Fujimoto–Belleau reaction
1275:List of organic reactions
1139:Negative hyperconjugation
884:
826:
143:–X → R–R
4043:Pictet–Spengler reaction
3958:Einhorn–Brunner reaction
3923:Boger pyridine synthesis
3817:Oxo-Diels–Alder reaction
3732:Aza-Diels–Alder reaction
3629:Pictet–Spengler reaction
3529:Hofmann–Löffler reaction
3519:Hegedus indole synthesis
3489:Fischer indole synthesis
3364:Bartoli indole synthesis
3319:Willgerodt rearrangement
3149:McLafferty rearrangement
3059:Ferrier carbocyclization
2874:2,3-Wittig rearrangement
2864:1,2-Wittig rearrangement
2704:Parikh–Doering oxidation
2694:Oxygen rebound mechanism
2359:Adkins–Peterson reaction
2251:Yamaguchi esterification
2191:Hegedus indole synthesis
2156:Bartoli indole synthesis
2027:Bamford–Stevens reaction
1943:Weinreb ketone synthesis
1903:Stork enamine alkylation
1678:Knoevenagel condensation
1548:Ferrier carbocyclization
1438:Castro–Stephens coupling
1064:Hammett acidity function
1054:Free-energy relationship
999:Curtin–Hammett principle
984:Conformational isomerism
770:10.1002/recl.19360551003
375:Johns Hopkins University
177:CuLi, R = 1°, 2°, or 3°
4003:Knorr pyrrole synthesis
3938:Bucherer–Bergs reaction
3883:Allan–Robinson reaction
3862:Wagner-Jauregg reaction
3654:Ring-closing metathesis
3579:Larock indole synthesis
3559:Knorr pyrrole synthesis
3414:Bucherer–Bergs reaction
3279:Stieglitz rearrangement
3259:Skattebøl rearrangement
3229:Ring-closing metathesis
3089:Group transfer reaction
3054:Favorskii rearrangement
2994:Cornforth rearrangement
2924:Bamberger rearrangement
2829:Wolff–Kishner reduction
2649:Markó–Lam deoxygenation
2544:Fleming–Tamao oxidation
2539:Fischer–Tropsch process
2226:Oxymercuration reaction
2206:Knorr pyrrole synthesis
2032:Barton–Kellogg reaction
1938:Wagner-Jauregg reaction
1858:Ring-closing metathesis
1848:Reimer–Tiemann reaction
1838:Rauhut–Currier reaction
1753:Nef isocyanide reaction
1713:Malonic ester synthesis
1683:Knorr pyrrole synthesis
1618:High dilution principle
1553:Friedel–Crafts reaction
1488:Cross-coupling reaction
1413:Bucherer–Bergs reaction
1398:Blanc chloromethylation
1388:Blaise ketone synthesis
1363:Baylis–Hillman reaction
1358:Barton–Kellogg reaction
1333:Allan–Robinson reaction
1239:Woodward–Hoffmann rules
974:Charge-transfer complex
246:) is prepared from the
230:R–X + 2 Li° → RLi + LiX
3968:Feist–Benary synthesis
3742:Bradsher cycloaddition
3712:4+4 Photocycloaddition
3669:Simmons–Smith reaction
3614:Paternò–Büchi reaction
3474:Feist–Benary synthesis
3464:Dieckmann condensation
3214:Pummerer rearrangement
3194:Oxy-Cope rearrangement
3169:Myers allene synthesis
3119:Jacobsen rearrangement
3034:Electrocyclic reaction
3009:Demjanov rearrangement
2964:Buchner ring expansion
2934:Beckmann rearrangement
2914:Aza-Cope rearrangement
2909:Arndt–Eistert reaction
2884:Alkyne zipper reaction
2804:Transfer hydrogenation
2779:Sharpless oxyamination
2754:Selenoxide elimination
2639:Lombardo methylenation
2564:Griesbaum coozonolysis
2474:Corey–Itsuno reduction
2449:Boyland–Sims oxidation
2389:Angeli–Rimini reaction
2037:Boord olefin synthesis
1981:Arndt–Eistert reaction
1973:Homologation reactions
1773:Nitro-Mannich reaction
1688:Kolbe–Schmitt reaction
1498:Cross-coupling partner
1418:Buchner ring expansion
1338:Arndt–Eistert reaction
1104:Kinetic isotope effect
851:Rearrangement reaction
691:10.1002/anie.197400821
652:Kochi, Jay K. (1978).
339:
307:
258:2 RLi + CuI → Li + LiI
236:lithium dialkylcuprate
234:In the second step, a
162:metal–halogen exchange
121:
78:
3827:Pauson–Khand reaction
3664:Sharpless epoxidation
3619:Pechmann condensation
3499:Friedländer synthesis
3449:Davis–Beirut reaction
3304:Wallach rearrangement
3274:Stevens rearrangement
3209:Pinacol rearrangement
3189:Overman rearrangement
3104:Hofmann rearrangement
3099:Hayashi rearrangement
3064:Ferrier rearrangement
3019:Dimroth rearrangement
3004:Curtius rearrangement
2999:Criegee rearrangement
2979:Claisen rearrangement
2969:Carroll rearrangement
2904:Amadori rearrangement
2894:Allylic rearrangement
2774:Sharpless epoxidation
2509:Dess–Martin oxidation
2434:Bohn–Schmidt reaction
2294:Hofmann rearrangement
2097:Kauffmann olefination
2020:Olefination reactions
1958:Wurtz–Fittig reaction
1793:Palladium–NHC complex
1673:Kauffmann olefination
1628:Homologation reaction
1478:Corey–House synthesis
1458:Claisen rearrangement
1254:Yukawa–Tsuno equation
1214:Swain–Lupton equation
1194:Spherical aromaticity
1129:Möbius–Hückel concept
914:Aromatic ring current
876:Substitution reaction
338:
306:
244:Iowa State University
122:
79:
32:Corey–House synthesis
4033:Paal–Knorr synthesis
3903:Barton–Zard reaction
3847:Staudinger synthesis
3797:Ketene cycloaddition
3767:Diels–Alder reaction
3747:Cheletropic reaction
3727:Alkyne trimerisation
3609:Paal–Knorr synthesis
3574:Kulinkovich reaction
3549:Jacobsen epoxidation
3469:Diels–Alder reaction
3264:Smiles rearrangement
3254:Sigmatropic reaction
3139:Lossen rearrangement
2989:Corey–Fuchs reaction
2954:Boekelheide reaction
2949:Bergmann degradation
2879:Achmatowicz reaction
2664:Methionine sulfoxide
2464:Clemmensen reduction
2424:Bergmann degradation
2354:Acyloin condensation
2319:Strecker degradation
2274:Bergmann degradation
2241:Ullmann condensation
2107:Peterson olefination
2082:Hydrazone iodination
2062:Elimination reaction
1963:Zincke–Suhl reaction
1883:Sonogashira coupling
1843:Reformatsky reaction
1803:Peterson olefination
1768:Nierenstein reaction
1698:Kulinkovich reaction
1513:Diels–Alder reaction
1473:Corey–Fuchs reaction
1453:Claisen condensation
1323:Alkyne trimerisation
1298:Acyloin condensation
1264:Σ-bishomoaromaticity
1224:Thorpe–Ingold effect
836:Elimination reaction
631:10.1055/s-1971-35043
381:George M. Whitesides
147:+ "R–Cu" + LiX
96:
53:
4053:Prilezhaev reaction
4038:Pellizzari reaction
3717:(4+3) cycloaddition
3684:Van Leusen reaction
3659:Robinson annulation
3644:Pschorr cyclization
3639:Prilezhaev reaction
3369:Bergman cyclization
3324:Wolff rearrangement
3309:Weerman degradation
3199:Pericyclic reaction
3179:Neber rearrangement
3074:Fries rearrangement
2959:Brook rearrangement
2944:Bergman cyclization
2789:Staudinger reaction
2734:Rosenmund reduction
2724:Reductive amination
2689:Oppenauer oxidation
2479:Corey–Kim oxidation
2454:Cannizzaro reaction
2329:Weerman degradation
2304:Isosaccharinic acid
2216:Mukaiyama hydration
2072:Hofmann elimination
2057:Dehydrohalogenation
2042:Chugaev elimination
1863:Robinson annulation
1808:Pfitzinger reaction
1578:Gattermann reaction
1523:Wulff–Dötz reaction
1503:Dakin–West reaction
1428:Carbonyl allylation
1373:Bergman cyclization
1159:Kennedy J. P. Orton
1079:Hammond's postulate
1049:Flippin–Lodge angle
1019:Electromeric effect
944:Beta-silicon effect
929:Baker–Nathan effect
721:(27): 11124–11127.
578:10.1021/ja01045a049
522:for cases where an
506:10.1021/jo01348a012
479:10.1021/ja00991a049
211:palladium catalysis
69:
3802:McCormack reaction
3752:Conia-ene reaction
3584:Madelung synthesis
3374:Biginelli reaction
3164:Mumm rearrangement
3049:Favorskii reaction
2984:Cope rearrangement
2974:Chan rearrangement
2739:Rubottom oxidation
2669:Miyaura borylation
2634:Lipid peroxidation
2629:Lindgren oxidation
2609:Kornblum oxidation
2604:Kolbe electrolysis
2549:Fukuyama reduction
2459:Carbonyl reduction
2309:Marker degradation
2171:Diazonium compound
2161:Boudouard reaction
2140:Carbon-heteroatom
2067:Grieco elimination
1853:Rieche formylation
1798:Passerini reaction
1728:Meerwein arylation
1648:Hydroxymethylation
1543:Favorskii reaction
1443:Chan rearrangement
1378:Biginelli reaction
1303:Aldol condensation
1149:2-Norbornyl cation
1124:Möbius aromaticity
1119:Markovnikov's rule
1014:Effective molarity
959:Bürgi–Dunitz angle
949:Bicycloaromaticity
365:Harvard University
340:
308:
250:by treatment with
117:
74:
57:
4094:
4093:
4090:
4089:
4086:
4085:
4078:Wohl–Aue reaction
3722:6+4 Cycloaddition
3539:Iodolactonization
2859:1,2-rearrangement
2824:Wohl–Aue reaction
2744:Sabatier reaction
2709:Pinnick oxidation
2674:Mozingo reduction
2619:Leuckart reaction
2574:Haloform reaction
2489:Criegee oxidation
2469:Collins oxidation
2419:Benkeser reaction
2414:Bechamp reduction
2384:Andrussow process
2369:Alcohol oxidation
2279:Edman degradation
2186:Haloform reaction
2135:
2134:
2122:Takai olefination
2087:Julia olefination
1913:Takai olefination
1788:Olefin metathesis
1663:Julia olefination
1588:Grignard reaction
1568:Fukuyama coupling
1483:Coupling reaction
1448:Chan–Lam coupling
1318:Alkyne metathesis
1313:Alkane metathesis
1169:Phosphaethynolate
1074:George S. Hammond
1034:Electronic effect
989:Conjugated system
871:Stereospecificity
866:Stereoselectivity
831:Addition reaction
820:organic reactions
727:10.1021/ja304848n
663:978-0-12-418250-9
572:(17): 4871–4882.
500:(10): 3128–3141.
473:(15): 3911–3912.
434:Organic Reactions
325:Grignard reagents
315:Catalytic version
115:
103:
72:
60:
34:(also called the
27:Chemical reaction
16:(Redirected from
4119:
4073:Wenker synthesis
4063:Stollé synthesis
3918:Bobbitt reaction
3888:Auwers synthesis
3832:Povarov reaction
3757:Cyclopropanation
3695:
3689:Wenker synthesis
3444:Darzens reaction
3394:Bobbitt reaction
3239:Schmidt reaction
3044:Enyne metathesis
2819:Whiting reaction
2814:Wharton reaction
2759:Shapiro reaction
2749:Sarett oxidation
2714:Prévost reaction
2524:Emde degradation
2334:Wohl degradation
2314:Ruff degradation
2284:Emde degradation
2181:Grignard reagent
2117:Shapiro reaction
2102:McMurry reaction
1969:
1933:Ullmann reaction
1898:Stollé synthesis
1888:Stetter reaction
1878:Shapiro reaction
1868:Sakurai reaction
1763:Negishi coupling
1743:Minisci reaction
1738:Michael reaction
1723:McMurry reaction
1718:Mannich reaction
1598:Hammick reaction
1593:Grignard reagent
1533:Enyne metathesis
1518:Doebner reaction
1508:Darzens reaction
1353:Barbier reaction
1343:Auwers synthesis
1270:
1244:Woodward's rules
1209:Superaromaticity
1199:Spiroaromaticity
1099:Inductive effect
1094:Hyperconjugation
1069:Hammett equation
1009:Edwards equation
861:Regioselectivity
812:
805:
798:
789:
782:
781:
753:
747:
746:
709:
703:
702:
674:
668:
667:
649:
643:
642:
614:
608:
596:
590:
589:
561:
552:
551:
533:
527:
516:
510:
509:
489:
483:
482:
462:
456:
455:
429:
391:Herbert O. House
252:copper(I) iodide
157:Grignard reagent
146:
142:
127:) to form a new
126:
124:
123:
118:
116:
113:
112:
107:
101:
83:
81:
80:
75:
73:
70:
68:
65:
58:
47:diorganylcuprate
40:organic reaction
21:
4127:
4126:
4122:
4121:
4120:
4118:
4117:
4116:
4097:
4096:
4095:
4082:
3983:Gewald reaction
3866:
3693:
3674:Skraup reaction
3509:Graham reaction
3504:Gewald reaction
3335:
3328:
2850:
2843:
2799:Swern oxidation
2784:Stahl oxidation
2729:Riley oxidation
2684:Omega oxidation
2644:Luche reduction
2594:Jones oxidation
2559:Glycol cleavage
2554:Ganem oxidation
2499:Davis oxidation
2494:Dakin oxidation
2429:Birch reduction
2379:Amide reduction
2345:
2338:
2299:Hooker reaction
2261:
2255:
2143:
2141:
2131:
2127:Wittig reaction
2015:
2011:Wittig reaction
1986:Hooker reaction
1967:
1948:Wittig reaction
1923:Thorpe reaction
1908:Suzuki reaction
1893:Stille reaction
1828:Quelet reaction
1703:Kumada coupling
1653:Ivanov reaction
1643:Hydrovinylation
1623:Hiyama coupling
1583:Glaser coupling
1393:Blaise reaction
1383:Bingel reaction
1368:Benary reaction
1285:
1283:
1277:
1268:
1164:Passive binding
1084:Homoaromaticity
934:Baldwin's rules
909:Antiaromaticity
904:Anomeric effect
880:
822:
816:
786:
785:
764:(10): 821–834.
755:
754:
750:
711:
710:
706:
676:
675:
671:
664:
651:
650:
646:
616:
615:
611:
597:
593:
563:
562:
555:
548:
535:
534:
530:
517:
513:
491:
490:
486:
464:
463:
459:
452:
431:
430:
426:
421:
404:
353:
330:catalytic cycle
317:
298:
287:
283:
279:
219:
176:
171:
144:
140:
100:
94:
93:
51:
50:
28:
23:
22:
15:
12:
11:
5:
4125:
4123:
4115:
4114:
4112:Name reactions
4109:
4099:
4098:
4092:
4091:
4088:
4087:
4084:
4083:
4081:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4020:
4015:
4010:
4005:
4000:
3995:
3990:
3988:Hantzsch ester
3985:
3980:
3975:
3970:
3965:
3960:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3898:Banert cascade
3895:
3890:
3885:
3880:
3874:
3872:
3868:
3867:
3865:
3864:
3859:
3854:
3849:
3844:
3839:
3837:Prato reaction
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3789:
3784:
3779:
3774:
3769:
3764:
3759:
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3703:
3701:
3692:
3691:
3686:
3681:
3676:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3340:
3338:
3330:
3329:
3327:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3216:
3211:
3206:
3201:
3196:
3191:
3186:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2929:Banert cascade
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2855:
2853:
2849:Rearrangement
2845:
2844:
2842:
2841:
2839:Zinin reaction
2836:
2831:
2826:
2821:
2816:
2811:
2809:Wacker process
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:
2651:
2646:
2641:
2636:
2631:
2626:
2621:
2616:
2611:
2606:
2601:
2596:
2591:
2586:
2584:Hydrogenolysis
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2534:Étard reaction
2531:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2439:Bosch reaction
2436:
2431:
2426:
2421:
2416:
2411:
2406:
2401:
2396:
2391:
2386:
2381:
2376:
2371:
2366:
2361:
2356:
2350:
2348:
2344:Organic redox
2340:
2339:
2337:
2336:
2331:
2326:
2321:
2316:
2311:
2306:
2301:
2296:
2291:
2286:
2281:
2276:
2271:
2265:
2263:
2257:
2256:
2254:
2253:
2248:
2243:
2238:
2233:
2228:
2223:
2218:
2213:
2208:
2203:
2198:
2193:
2188:
2183:
2178:
2176:Esterification
2173:
2168:
2163:
2158:
2153:
2147:
2145:
2137:
2136:
2133:
2132:
2130:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2023:
2021:
2017:
2016:
2014:
2013:
2008:
2003:
1998:
1993:
1988:
1983:
1977:
1975:
1966:
1965:
1960:
1955:
1953:Wurtz reaction
1950:
1945:
1940:
1935:
1930:
1925:
1920:
1915:
1910:
1905:
1900:
1895:
1890:
1885:
1880:
1875:
1870:
1865:
1860:
1855:
1850:
1845:
1840:
1835:
1830:
1825:
1823:Prins reaction
1820:
1815:
1810:
1805:
1800:
1795:
1790:
1785:
1780:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1655:
1650:
1645:
1640:
1638:Hydrocyanation
1635:
1630:
1625:
1620:
1615:
1610:
1608:Henry reaction
1605:
1600:
1595:
1590:
1585:
1580:
1575:
1570:
1565:
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1475:
1470:
1465:
1460:
1455:
1450:
1445:
1440:
1435:
1430:
1425:
1420:
1415:
1410:
1405:
1400:
1395:
1390:
1385:
1380:
1375:
1370:
1365:
1360:
1355:
1350:
1345:
1340:
1335:
1330:
1325:
1320:
1315:
1310:
1308:Aldol reaction
1305:
1300:
1295:
1289:
1287:
1282:Carbon-carbon
1279:
1278:
1273:
1267:
1266:
1261:
1259:Zaitsev's rule
1256:
1251:
1246:
1241:
1236:
1231:
1226:
1221:
1216:
1211:
1206:
1204:Steric effects
1201:
1196:
1191:
1186:
1181:
1176:
1171:
1166:
1161:
1156:
1151:
1146:
1141:
1136:
1131:
1126:
1121:
1116:
1111:
1106:
1101:
1096:
1091:
1086:
1081:
1076:
1071:
1066:
1061:
1056:
1051:
1046:
1041:
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
981:
976:
971:
966:
961:
956:
951:
946:
941:
936:
931:
926:
921:
916:
911:
906:
901:
896:
891:
885:
882:
881:
879:
878:
873:
868:
863:
858:
856:Redox reaction
853:
848:
843:
841:Polymerization
838:
833:
827:
824:
823:
817:
815:
814:
807:
800:
792:
784:
783:
748:
704:
669:
662:
644:
625:(6): 303–305.
609:
591:
553:
547:978-0471984160
546:
528:
520:Wurtz coupling
511:
484:
457:
451:978-0471264187
450:
423:
422:
420:
417:
416:
415:
413:Wurtz reaction
410:
408:Gilman reagent
403:
400:
399:
398:
388:
378:
371:Gary H. Posner
368:
352:
349:
323:reported that
316:
313:
296:
285:
281:
277:
273:
272:
260:
259:
232:
231:
218:
215:
174:
170:
167:
149:
148:
111:
106:
86:organic halide
64:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4124:
4113:
4110:
4108:
4105:
4104:
4102:
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:
3998:Herz reaction
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:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3875:
3873:
3869:
3863:
3860:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3704:
3702:
3700:
3699:Cycloaddition
3696:
3690:
3687:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3544:Isay reaction
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3439:Cycloaddition
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3341:
3339:
3337:
3334:Ring forming
3331:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3234:Rupe reaction
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3170:
3167:
3165:
3162:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
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:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2856:
2854:
2852:
2846:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
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:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2624:Ley oxidation
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2589:Hydroxylation
2587:
2585:
2582:
2580:
2579:Hydrogenation
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2514:DNA oxidation
2512:
2510:
2507:
2505:
2504:Deoxygenation
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2427:
2425:
2422:
2420:
2417:
2415:
2412:
2410:
2407:
2405:
2402:
2400:
2397:
2395:
2394:Aromatization
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2351:
2349:
2347:
2341:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2277:
2275:
2272:
2270:
2267:
2266:
2264:
2258:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2231:Reed reaction
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2148:
2146:
2142:bond forming
2138:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2047:Cope reaction
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2024:
2022:
2018:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1979:
1978:
1976:
1974:
1970:
1964:
1961:
1959:
1956:
1954:
1951:
1949:
1946:
1944:
1941:
1939:
1936:
1934:
1931:
1929:
1926:
1924:
1921:
1919:
1916:
1914:
1911:
1909:
1906:
1904:
1901:
1899:
1896:
1894:
1891:
1889:
1886:
1884:
1881:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1856:
1854:
1851:
1849:
1846:
1844:
1841:
1839:
1836:
1834:
1831:
1829:
1826:
1824:
1821:
1819:
1816:
1814:
1811:
1809:
1806:
1804:
1801:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1758:Nef synthesis
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1733:Methylenation
1731:
1729:
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1603:Heck reaction
1601:
1599:
1596:
1594:
1591:
1589:
1586:
1584:
1581:
1579:
1576:
1574:
1571:
1569:
1566:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1421:
1419:
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1399:
1396:
1394:
1391:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1369:
1366:
1364:
1361:
1359:
1356:
1354:
1351:
1349:
1346:
1344:
1341:
1339:
1336:
1334:
1331:
1329:
1326:
1324:
1321:
1319:
1316:
1314:
1311:
1309:
1306:
1304:
1301:
1299:
1296:
1294:
1291:
1290:
1288:
1284:bond forming
1280:
1276:
1271:
1265:
1262:
1260:
1257:
1255:
1252:
1250:
1249:Y-aromaticity
1247:
1245:
1242:
1240:
1237:
1235:
1234:Walsh diagram
1232:
1230:
1227:
1225:
1222:
1220:
1219:Taft equation
1217:
1215:
1212:
1210:
1207:
1205:
1202:
1200:
1197:
1195:
1192:
1190:
1189:Σ-aromaticity
1187:
1185:
1182:
1180:
1177:
1175:
1172:
1170:
1167:
1165:
1162:
1160:
1157:
1155:
1152:
1150:
1147:
1145:
1142:
1140:
1137:
1135:
1132:
1130:
1127:
1125:
1122:
1120:
1117:
1115:
1114:Marcus theory
1112:
1110:
1107:
1105:
1102:
1100:
1097:
1095:
1092:
1090:
1089:Hückel's rule
1087:
1085:
1082:
1080:
1077:
1075:
1072:
1070:
1067:
1065:
1062:
1060:
1057:
1055:
1052:
1050:
1047:
1045:
1044:Evelyn effect
1042:
1040:
1037:
1035:
1032:
1030:
1027:
1025:
1024:Electron-rich
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
995:
992:
990:
987:
985:
982:
980:
977:
975:
972:
970:
967:
965:
962:
960:
957:
955:
952:
950:
947:
945:
942:
940:
939:Bema Hapothle
937:
935:
932:
930:
927:
925:
922:
920:
917:
915:
912:
910:
907:
905:
902:
900:
897:
895:
892:
890:
887:
886:
883:
877:
874:
872:
869:
867:
864:
862:
859:
857:
854:
852:
849:
847:
844:
842:
839:
837:
834:
832:
829:
828:
825:
821:
813:
808:
806:
801:
799:
794:
793:
790:
779:
775:
771:
767:
763:
759:
752:
749:
744:
740:
736:
732:
728:
724:
720:
716:
708:
705:
700:
696:
692:
688:
684:
680:
673:
670:
665:
659:
655:
648:
645:
640:
636:
632:
628:
624:
620:
613:
610:
606:
602:
595:
592:
587:
583:
579:
575:
571:
567:
560:
558:
554:
549:
543:
539:
532:
529:
525:
521:
518:However, see
515:
512:
507:
503:
499:
495:
488:
485:
480:
476:
472:
468:
461:
458:
453:
447:
443:
439:
435:
428:
425:
418:
414:
411:
409:
406:
405:
401:
396:
392:
389:
386:
382:
379:
376:
372:
369:
366:
362:
359:
358:
357:
350:
348:
345:
337:
333:
331:
326:
322:
314:
312:
305:
301:
293:
289:
280:)CuM, where R
270:
269:
268:
264:
257:
256:
255:
253:
249:
245:
241:
237:
229:
228:
227:
225:
216:
214:
212:
208:
204:
200:
196:
192:
188:
184:
180:
168:
166:
163:
158:
154:
153:organolithium
138:
137:
136:
134:
130:
109:
104:
91:
87:
62:
48:
45:
41:
37:
33:
19:
3039:Ene reaction
2399:Autoxidation
2260:Degradation
2151:Azo coupling
1928:Ugi reaction
1528:Ene reaction
1477:
1328:Alkynylation
1179:Polyfluorene
1174:Polar effect
1039:Electrophile
954:Bredt's rule
924:Baird's rule
894:Alpha effect
761:
757:
751:
718:
714:
707:
685:(1): 82–83.
682:
678:
672:
653:
647:
622:
618:
612:
604:
600:
594:
569:
565:
537:
531:
523:
514:
497:
493:
487:
470:
466:
460:
433:
427:
354:
341:
318:
309:
294:
290:
274:
265:
261:
248:alkyllithium
240:Henry Gilman
233:
224:alkyllithium
220:
172:
150:
133:organocopper
90:pseudohalide
35:
31:
29:
1538:Ethenolysis
1184:Ring strain
1154:Nucleophile
979:Clar's rule
919:Aromaticity
139:Li + R
4101:Categories
3822:Ozonolysis
3349:Annulation
2699:Ozonolysis
818:Topics in
419:References
361:E.J. Corey
351:Background
84:) with an
3336:reactions
2851:reactions
2346:reactions
2262:reactions
2144:reactions
1286:reactions
778:0165-0513
735:0002-7863
699:1521-3773
639:0039-7881
619:Synthesis
586:0002-7863
321:Jay Kochi
319:In 1971,
110:−
1229:Vinylogy
899:Annulene
846:Reagents
743:22734716
402:See also
195:benzylic
105:′
889:A value
524:in situ
199:allylic
187:alkenyl
44:lithium
776:
741:
733:
697:
660:
637:
584:
544:
448:
191:methyl
129:alkane
344:TMEDA
205:, or
185:, or
179:alkyl
169:Scope
774:ISSN
739:PMID
731:ISSN
695:ISSN
658:ISBN
635:ISSN
623:1971
582:ISSN
542:ISBN
446:ISBN
183:aryl
71:CuLi
30:The
766:doi
723:doi
719:134
687:doi
627:doi
574:doi
502:doi
475:doi
438:doi
332:.
242:of
207:OTf
203:OTs
155:or
88:or
4103::
772:.
762:55
760:.
737:.
729:.
717:.
693:.
683:13
681:.
633:.
621:.
580:.
570:91
568:.
556:^
498:31
496:.
471:89
469:.
444:.
213:.
197:,
193:,
181:,
811:e
804:t
797:v
780:.
768::
745:.
725::
701:.
689::
666:.
641:.
629::
605:S
601:R
599:(
588:.
576::
550:.
508:.
504::
481:.
477::
454:.
440::
397:)
383:(
373:(
363:(
297:N
286:U
282:U
278:U
175:2
145:′
141:′
114:X
102:R
92:(
63:2
59:R
49:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
