Abstract
During the last decades a powerful set of protocols featuring C(sp2)–N bond formation have emerged as convenient alternatives for the assembly of enamine and enamides. Those methods consist of mostly palladium-catalyzed oxidative amidations of alkenes and both palladium- and copper-catalyzed cross-couplings between generally vinyl halides or pseudohalides and amines or amides. In this review recent advances in both types of processes will be disclosed. Additionally, the synthetic value of the title processes will be illustrated by describing relevant total syntheses of natural products involving vinylation process as the key step.
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References
Yet L (2003) Chem Rev 103:4283
Carbery DR (2008) Org Biomol Chem 6:3455
Dake GR (2012) Synlett: 814
Satyanarayana G, Maier ME (2008) J Org Chem 73:5410
Harrison P, Meek G (2004) Tetrahedron Lett 45:9277
Liu Y, Li D, Park CM (2011) Angew Chem Int Ed 50:7333
Nguyen TB, Martel A, Dhal R, Dujardin G (2008) J Org Chem 73:2621
Zhou H, Xu YH, Chung WJ, Loh TP (2009) Angew Chem Int Ed 48:5355
Zhou H, Chung WJ, Xu YH, Loh TP (2009) Chem Commun: 3472
Pankajakshan S, Xu YH, Cheng JK, Low MT, Loh TP (2012) Angew Chem Int Ed 51:5701
Gigant N, Gillaizeau I (2012) Org Lett 14:3304
Cheung CW, Buchwald SL (2012) J Org Chem 77:7526
Hesp KD, Bergman RG, Ellman JA (2011) J Am Chem Soc 133:11430
Phipps RJ, Hiramatsu K, Toste FD (2012) J Am Chem Soc 134:8376
Toumi M, Couty F, Evano G (2008) J Org Chem 73:1270
Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Ruthjes FPJT (2001) Org Lett 3:2045
Berthiol F, Matsubara R, Kawai N, Kobayashi S (2007) Angew Chem Int Ed 46:7803
Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471
Matsubara R, Kobayashi S (2008) Acc Chem Res 41:292
Genovino J, Lagu B, Wang Y, Toure BB (2012) Chem Commun: 6735
Reeves JT, Tan Z, Han ZS, Li G, Zhang Y, Xu Y, Reeves DC, Gonnella NC, Ma S, Lee H, Lu BZ, Senanayake CH (2012) Angew Chem Int Ed 51:1400
Severin R, Doye S (2007) Chem Soc Rev 36:1407
Arndt M, Salih KSM, Fromm A, Goossen LJ, Menges F, Niedner-Schatteburg G (2011) J Am Chem Soc 133:7428
Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem Commun: 2060
Bolig AD, Brookhart M (2007) J Am Chem Soc 129:14544
Kondo T, Tanaka A, Kotachi S, Watanabe Y (1995) J Chem Soc Chem Commun: 413
Goossen LJ, Rauhaus JE, Deng G (2005) Angew Chem Int Ed 44:4402
Goossen LJ, Arndt M, Blanchot M, Rudolphi F, Menges F, Niedner-Schatteburg G (2008) Adv Synth Catal 350:2701
Yudha SS, Kuninobu Y, Takai K (2007) Org Lett 9:5609
Stille JK, Becker Y (1980) J Org Chem 45:2139
Sergeyev S, Hesse M (2002) Synlett: 1313
Krompiec S, Pigulla M, Krompiec M, Baj S, Mrowiec-Bialón J, Kasperczyk J (2004) Tetrahedron Lett 45:5257
Tsujita H, Ura Y, Matsuki S, Wada K, Mitsudo T, Kondo T (2007) Angew Chem Int Ed 46:5160
Zhao H, Vandenbossche CP, Koenig SG, Singh SP, Bakale RP (2008) Org Lett 10:505
Guan ZH, Zhang ZY, Ren ZH, Wang YY, Zhang X (2011) J Org Chem 76:339
Villa MVJ, Targett SM, Barnes JC, Whittingham WG, Marquez R (2007) Org Lett 9:1631
Lu Z, Kong W, Yuan Z, Zhao X, Zhu G (2011) J Org Chem 76:8524
Beccalli EM, Broggini G, Martinelli M, Sottocornola S (2007) Chem Rev 107:5318
Barluenga J, Valdés C (2005) Chem Commun: 4891
Dehli JR, Legros J, Bolm C (2005) Chem Commun: 973
Hosokawa T, Takano M, Kuroki Y, Murahashi SI (1992) Tetrahedron Lett 33:6643
Lee JM, Ahn DS, Jung DY, Lee J, Do Y, Kim SK, Chang S (2006) J Am Chem Soc 128:12954
Kotov V, Scarborough CC, Stahl SS (2007) Inorg Chem 46:1910
Timokhin VI, Anastasi NR, Stahl SS (2003) J Am Chem Soc 125:12996
Timokhin VI, Stahl SS (2005) J Am Chem Soc 127:17888
Brice JL, Harang JE, Timokhin VI, Anastasi NR, Stahl SS (2005) J Am Chem Soc 127:2868
Rogers MM, Kotov V, Chatwichien J, Stahl SS (2007) Org Lett 9:4331
Brice JL, Meerdink JE, Stahl SS (2004) Org Lett 6:1845
Beller M, Eichberger M, Trauthwein H (1997) Angew Chem Int Ed Engl 36:2225
Beller M, Trauthwein H, Eichberger M, Breindl C, Herwig J, Müller TE, Thiel OR (1999) Chem Eur J 5:1306
Schlummer B, Scholz U (2004) Adv Synth Catal 346:1599
Buchwald SL, Mauger C, Mignani G, Scholz U (2006) Adv Synth Catal 348:23
Corbet JP, Mignani G (2006) Chem Rev 106:2651
Yang B, Buchwald SL (1999) J Organomet Chem 576:125
Surry DS, Buchwald SL (2008) Angew Chem Int Ed 47:6338
Hicks FA, Brookhart M (2000) Org Lett 2:219
Jutand A, Négri S (2003) Organometallics 22:4229
Willis MC, Brace GN (2002) Tetrahedron Lett 43:9085
Lebedev AY, Izmir VV, Kazyul’kin DN, Beletskaya IP, Voskoboynikov AZ (2002) Org Lett 4:623
Movassaghi M, Ondrus AE (2005) J Org Chem 70:8638
Barluenga J, Fernández MA, Aznar F, Valdés C (2002) Chem Commun: 2362
Barluenga J, Fernández MA, Aznar F, Valdés C (2004) Chem Eur J 10:494
Barluenga J, Fernández MA, Aznar F, Valdés C (2004) Chem Commun: 1400
Barluenga J, Aznar F, Moriel P, Valdés C (2004) Adv Synth Catal 346:1697
Kozawa Y, Mori M (2002) Tetrahedron Lett 43:111
Kozawa Y, Mori M (2003) J Org Chem 68:3064
Wallace DJ, Klauber DJ, Chen CY, Volante RP (2003) Org Lett 5:4749
Klapars A, Campos KR, Chen CY, Volante RP (2005) Org Lett 7:1185
Willis MC, Brace GN, Colmes IP (2005) Synthesis: 3229
Tanoury GJ, Chen M, Dong Y, Forslund RE, Magdziak (2008) Org Lett 10:185
Barluenga J, Aznar F, Valdés C (2004) Angew Chem Int Ed 43:343
Barluenga J, Moriel P, Aznar F, Valdés C (2007) Org Lett 9:275
Delhi JR, Bolm C (2004) J Org Chem 69:8518
Hetzer RH, Gais H-J, Raabe G (2008) Synthesis: 1126
Dalili S, Yudin AK (2005) Org Lett 7:1161
Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400
Beletskaya IP, Cheprakov AV (2004) Coord Chem Rev 248:2337
Hartwig JF (2006) Synlett: 1283
Evano G, Blanchard N, Toumi M (2008) Chem Rev 108:3054
Monnier F, Taillefer M (2008) Angew Chem Int Ed 47:3096
Monnier F, Taillefer M (2009) Angew Chem Int Ed 48:6954
Taillefer M, Cristau HJ, Cellier PP, Ouali A, Spindler JF (2003) Patent FR 10,253 (WO 2005/023731 A2)
Correa A, Bolm C (2007) Adv Synth Catal 349:2673
Sperotto E, de Vries JG, Van Klink GPM, Van Koten G (2007) Tetrahedron Lett 48:7366
Zhu L, Guo P, Li G, Lan J, Xie R, You J (2007) J Org Chem 72:8535
Zhu R, Xing L, Wang X, Cheng C, Su D, Hu Y (2008) Adv Synth Catal 350:1253
Arterburn JB, Pannala M, Gonzalez AM (2001) Tetrahedron Lett 42:1475
Kiyomori A, Marcoux JF, Buchwald SL (1999) Tetrahedron Lett 40:2657
Lam PYS, Vincent G, Bonne D, Clark CG (2003) Tetrahedron Lett 44:4927
Wang Z, Bao W, Jiang Y (2005) Chem Commun: 2849
Shen G, Lv X, Qian W, Bao W (2008) Tetrahedron Lett 49:4556
Taillefer M, Cristau HJ, Cellier PP, Ouali A, Spindler JF (2002) Patent FR 06,717 (WO 031101966)
Cristau HJ, Cellier PP, Spindler JF, Taillefer M (2004) Eur J Org Chem: 695
Taillefer M, Ouali A, Renard B, Spindler JF (2006) Chem Eur J 12:5301
Ouali A, Laurent R, Caminade AM, Mayoral JP, Taillefer M (2006) J Am Chem Soc 128:15990
Mao J, Hua Q, Guo J, Shi D, Ji S (2008) Synlett: 2011
Mao J, Xie G, Zhan J, Hua Q, Shia D (2009) Adv Synth Catal 351:1268
Ogawa T, Kiji T, Hayami K, Suzuki H (1991) Chem Lett: 1443
Shen R, Porco JA Jr (2000) Org Lett 2:1333
Allred GD, Liebeskind LS (1996) J Am Chem Soc 118:2748
Zhang S, Zhang D, Liebeskind LS (1997) J Org Chem 62:2312
Han C, Shen R, Su S, Porco JA Jr (2004) Org Lett 6:27
Jiang L, Job GE, Klapars A, Buchwald SL (2003) Org Lett 5:3667
Cesati RR III, Dwyer G, Jones RC, Hayes MP, Yalamanchili P, Casebier DS (2007) Org Lett 9:5617
Rainka MP, Aye Y, Buchwald SL (2004) Proc Natl Acad Sci USA 101:5821
Pan X, Cai Q, Ma D (2004) Org Lett 6:1809
Coste A, Couty F, Evano G (2009) Org Lett 11:4454
Coste A, Karthikeyan G, Couty F, Evano G (2009) Angew Chem Int Ed 48:4381
Hu T, Li C (2005) Org Lett 7:2035
Lu H, Li C (2006) Org Lett 8:5365
Lu H, Yuan X, Zhu S, Sun C, Li C (2008) J Org Chem 73:8665
Zhao Q, Li C (2008) Org Lett 10:4040
Zhao Q, Li L, Fang Y, Sun D, Li C (2009) J Org Chem 74:459
Sun C, Fang Y, Li S, Zhang Y, Zhao Q, Zhu S, Li C (2009) Org Lett 11:4084
Chen L, Shi M, Li C (2008) Org Lett 10:5285
Trost BM, Stiles DT (2005) Org Lett 7:2117
Nishikawa T, Kajii S, Isobe M (2004) Chem Lett 33:440
Sun C, Camp JE, Weinreb SM (2006) Org Lett 8:1779
Sanapo GF, Daoust B (2008) Tetrahedron Lett 49:4196
Jiang B, Tian H, Huang ZG, Xu M (2008) Org Lett 10:2737
Schuh K, Glorius F (2007) Synthesis 15:2297
Bolshan Y, Batey RA (2008) Angew Chem Int Ed 47:2109
Bolshan Y, Batey RA (2010) Tetrahedron 66:5283
Arsenyan P, Petrenko A, Belyakov S (2008) Tetrahedron Lett 49:5255
Zhu W, Ma D (2004) Chem Commun: 888
Dehli JR, Bolm C (2005) Adv Synth Catal 347:239
Yang L, Deng G, Wang DX, Huang ZT, Zhu JP, Wang MX (2007) Org Lett 9:1387
Kabalka GW, Guchhait SK (2003) Org Lett 5:4129
Martín R, Rodríguez Rivero M, Buchwald SL (2006) Angew Chem Int Ed 45:7079
Rodríguez Rivero M, Buchwald SL (2007) Org Lett 9:973
Yuan X, Xu X, Zhou X, Yuan J, Mai L, Li Y (2007) J Org Chem 72:1510
Fürstner A, Dierkes T, Thiel OR, Blanda G (2001) Chem Eur J 7:5286
Nicolaou KC, Kim DW, Baati R (2002) Angew Chem Int Ed 41:3701
Nicolaou KC, Kim DW, Baati R, O’Brate A, Giannakakou P (2003) Chem Eur J 9:6177
Su Q, Panek JS (2004) J Am Chem Soc 126:2425
Shen R, Lin CT, Porco JA Jr (2002) J Am Chem Soc 124:5650
Shen R, Lin CT, Bowman EJ, Bowman BJ, Porco JA Jr (2003) J Am Chem Soc 125:7889
Wang X, Porco JA Jr (2003) J Am Chem Soc 125:6040
Coleman RS, Liu PH (2004) Org Lett 6:577
Dias LC, de Oliveira LG, Vilcachagua JD, Nigsh F (2005) J Org Chem 70:2225
Toumi M, Couty F, Evano G (2007) Angew Chem Int Ed 46:572
Toumi M, Couty F, Evano G (2007) J Org Chem 72:9003
Toumi M, Couty F, Evano G (2008) Synlett: 29
Wang J, Schaeffler L, He G, Ma D (2007) Tetrahedron Lett 48:6717
He G, Wang J, Ma D (2007) Org Lett 9:1367
Acknowledgments
A.C. thanks the Basque Government for being supported by “Programa de Perfeccionamiento de Doctores en el extranjero del Departamento de Educación, Universidades e Investigación.” The authors are also grateful to the Fonds der Chemischen Industrie for continuous support.
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Correa, A., Bolm, C. (2012). Metal-Catalyzed C(sp2)–N Bond Formation. In: Taillefer, M., Ma, D. (eds) Amination and Formation of sp2 C-N Bonds. Topics in Organometallic Chemistry, vol 46. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_57
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DOI: https://doi.org/10.1007/3418_2012_57
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