amination of alkenes and both palladium- and copper-catalyzed N-vinylation
of generally amines and amides stand out today as reliable and efficient protocols
for the assembly of such type of compounds. In particular, based on the mild
reaction conditions, broad functional group tolerance, and mostly the high degree
of stereospecificity, copper-catalyzed cross-couplings between vinyl halides and
amides have been broadly identified as the method of choice in the field of natural
product synthesis. Therefore, continued growth and advances of paramount synthetic
importance in the field can be anticipated.
Acknowledgments A.C. thanks the Basque Government for being supported by “Programa de
Perfeccionamiento de Doctores en el extranjero del Departamento de Educacio ´n, Universidades
e Investigacio ´n.” The authors are also grateful to the Fonds der Chemischen Industrie for
continuous support.
References
1. Yet L (2003) Chem Rev 103:4283
2. Carbery DR (2008) Org Biomol Chem 6:3455
3. Dake GR (2012) Synlett: 814
4. Satyanarayana G, Maier ME (2008) J Org Chem 73:5410
5. Harrison P, Meek G (2004) Tetrahedron Lett 45:9277
6. Liu Y, Li D, Park CM (2011) Angew Chem Int Ed 50:7333
7. Nguyen TB, Martel A, Dhal R, Dujardin G (2008) J Org Chem 73:2621
8. Zhou H, Xu YH, Chung WJ, Loh TP (2009) Angew Chem Int Ed 48:5355
9. Zhou H, Chung WJ, Xu YH, Loh TP (2009) Chem Commun: 3472
10. Pankajakshan S, Xu YH, Cheng JK, Low MT, Loh TP (2012) Angew Chem Int Ed 51:5701
11. Gigant N, Gillaizeau I (2012) Org Lett 14:3304
12. Cheung CW, Buchwald SL (2012) J Org Chem 77:7526
13. Hesp KD, Bergman RG, Ellman JA (2011) J Am Chem Soc 133:11430
14. Phipps RJ, Hiramatsu K, Toste FD (2012) J Am Chem Soc 134:8376
15. Toumi M, Couty F, Evano G (2008) J Org Chem 73:1270
16. Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Ruthjes FPJT (2001)
Org Lett 3:2045
17. Berthiol F, Matsubara R, Kawai N, Kobayashi S (2007) Angew Chem Int Ed 46:7803
18. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471
19. Matsubara R, Kobayashi S (2008) Acc Chem Res 41:292
20. Genovino J, Lagu B, Wang Y, Toure BB (2012) Chem Commun: 6735
21. 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
22. Severin R, Doye S (2007) Chem Soc Rev 36:1407
23. Arndt M, Salih KSM, Fromm A, Goossen LJ, Menges F, Niedner-Schatteburg G (2011)
J Am Chem Soc 133:7428
24. Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem Commun: 2060
25. Bolig AD, Brookhart M (2007) J Am Chem Soc 129:14544
26. Kondo T, Tanaka A, Kotachi S, Watanabe Y (1995) J Chem Soc Chem Commun: 413
27. Goossen LJ, Rauhaus JE, Deng G (2005) Angew Chem Int Ed 44:4402
28. Goossen LJ, Arndt M, Blanchot M, Rudolphi F, Menges F, Niedner-Schatteburg G (2008)
Adv Synth Catal 350:2701
82
A. Correa and C. Bolm
of generally amines and amides stand out today as reliable and efficient protocols
for the assembly of such type of compounds. In particular, based on the mild
reaction conditions, broad functional group tolerance, and mostly the high degree
of stereospecificity, copper-catalyzed cross-couplings between vinyl halides and
amides have been broadly identified as the method of choice in the field of natural
product synthesis. Therefore, continued growth and advances of paramount synthetic
importance in the field can be anticipated.
Acknowledgments A.C. thanks the Basque Government for being supported by “Programa de
Perfeccionamiento de Doctores en el extranjero del Departamento de Educacio ´n, Universidades
e Investigacio ´n.” The authors are also grateful to the Fonds der Chemischen Industrie for
continuous support.
References
1. Yet L (2003) Chem Rev 103:4283
2. Carbery DR (2008) Org Biomol Chem 6:3455
3. Dake GR (2012) Synlett: 814
4. Satyanarayana G, Maier ME (2008) J Org Chem 73:5410
5. Harrison P, Meek G (2004) Tetrahedron Lett 45:9277
6. Liu Y, Li D, Park CM (2011) Angew Chem Int Ed 50:7333
7. Nguyen TB, Martel A, Dhal R, Dujardin G (2008) J Org Chem 73:2621
8. Zhou H, Xu YH, Chung WJ, Loh TP (2009) Angew Chem Int Ed 48:5355
9. Zhou H, Chung WJ, Xu YH, Loh TP (2009) Chem Commun: 3472
10. Pankajakshan S, Xu YH, Cheng JK, Low MT, Loh TP (2012) Angew Chem Int Ed 51:5701
11. Gigant N, Gillaizeau I (2012) Org Lett 14:3304
12. Cheung CW, Buchwald SL (2012) J Org Chem 77:7526
13. Hesp KD, Bergman RG, Ellman JA (2011) J Am Chem Soc 133:11430
14. Phipps RJ, Hiramatsu K, Toste FD (2012) J Am Chem Soc 134:8376
15. Toumi M, Couty F, Evano G (2008) J Org Chem 73:1270
16. Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Ruthjes FPJT (2001)
Org Lett 3:2045
17. Berthiol F, Matsubara R, Kawai N, Kobayashi S (2007) Angew Chem Int Ed 46:7803
18. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471
19. Matsubara R, Kobayashi S (2008) Acc Chem Res 41:292
20. Genovino J, Lagu B, Wang Y, Toure BB (2012) Chem Commun: 6735
21. 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
22. Severin R, Doye S (2007) Chem Soc Rev 36:1407
23. Arndt M, Salih KSM, Fromm A, Goossen LJ, Menges F, Niedner-Schatteburg G (2011)
J Am Chem Soc 133:7428
24. Zhang X, Fried A, Knapp S, Goldman AS (2003) Chem Commun: 2060
25. Bolig AD, Brookhart M (2007) J Am Chem Soc 129:14544
26. Kondo T, Tanaka A, Kotachi S, Watanabe Y (1995) J Chem Soc Chem Commun: 413
27. Goossen LJ, Rauhaus JE, Deng G (2005) Angew Chem Int Ed 44:4402
28. Goossen LJ, Arndt M, Blanchot M, Rudolphi F, Menges F, Niedner-Schatteburg G (2008)
Adv Synth Catal 350:2701
82
A. Correa and C. Bolm