Palladium(II)-catalyzed direct alkenylation of nonaromatic enamides

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3304-3307

  Gigant, Nicolas ^a   Gillaizeau, Isabelle ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMIDES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84863616343     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301249n     Document Type: Article

References (57)

1. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083
2. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976-1991
3. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885-1898
4. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
5. Messaoudi, S.; Brion, J. D.; Alami, M. Eur. J. Org. Chem. 2010, 6495-6516
6. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
7. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
8. Dunn, P. J. Chem. Soc. Rev. 2012, 41, 1452-1461
9. Sheldon, R. A. Chem. Soc. Rev. 2012, 41, 1437-1451
10. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301-312
11. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010-3021
12. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40-49
13. Horvath, I. T.; Anastas, P. T. Chem. Rev. 2007, 107, 2167-2168
14. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489
15. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963
16. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066
17. Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119-1122
18. Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166-7169
19. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728-731
20. Li, Z.; Zhang, Y.; Liu, Z.-Q. Org. Lett. 2012, 14, 74-77
21. Zhang, Y.; Li, Z.; Liu, Z.-Q. Org. Lett. 2012, 14, 226-229
22. Xiang, S.-K.; Zhang, B.; Zhang, L.-H.; Cui, Y.; Jiao, N. Chem. Commun. 2011, 47, 8097-8099
23. Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170-1214
24. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
25. Kim, D.; Hong, S. Org. Lett. 2011, 13, 4466-4469
26. Ye, M.; Gao, G.-L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 6964-6967
27. Garcia-Rubia, A.; Fernandez-Ibanez, M.; Gomez Arrayas, R.; Carretero, J. C. Chem.-Eur. J. 2011, 17, 3567-3570
28. Nishikata, T.; Lipshutz, B. H. Org. Lett. 2010, 12, 1972-1975
29. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254-9256
30. Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528-2529
31. Grimster, M. P.; Gaunlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125-3129
32. Pankajakshan, S.; Xu, Y.-H.; Chang, J. K.; Low, M. T.; Loh, T. P. Angew. Chem., Int. Ed. 2012, 51, 1-6
33. Yu, Y.-Y.; Niphakis, M. J.; Georg., G. I. Org. Lett. 2011, 13, 5932-5935
34. Bai, Y.; Zeng, J.; Cai, S.; Liu, X.-W. Org. Lett. 2011, 13, 4394-4397
35. Yu, H.; Jin, W.; Sun, J.; Du, W.; He, S.; Yu, Z. Angew. Chem., Int. Ed. 2010, 49, 5792-5797
36. Xu, Y.-H.; Wang, W.-J.; Wen, Z.-K.; Hartley, J. J.; Loh, T.-P. Tetrahedron Lett. 2010, 51, 3504-3507
37. Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2009, 131, 1372-1373
38. Gigant, N.; Claveau, E.; Bouyssou, P.; Gillaizeau, I. Org. Lett. 2012, 14, 844-847
39. Gigant, N.; Dequirez, G.; Retailleau, P.; Gillaizeau, I.; Dauban, P. Chem.-Eur. J. 2012, 18, 90-94
40. Claveau, E.; Gillaizeau, I.; Kalinowska, J.; Bouyssou, P.; Coudert, G. J. Org. Chem. 2009, 74, 2911-2914
41. Claveau, E.; Gillaizeau, I.; Bruel, A.; Coudert, G. J. Org. Chem. 2007, 72, 4832-4836
42. Mousset, D.; Gillaizeau, I.; Sabatié, A.; Bouyssou, P.; Coudert, G. J. Org. Chem. 2006, 71, 5993-5999
43. Gopalaiah, K.; Kagan, H. B. Chem. Rev. 2011, 111, 4599-4657
44. Matsubara, R.; Kobayashi, S. Acc. Chem. Res. 2008, 41, 292-301
45. Carbery, D. R. Org. Biomol. Chem. 2008, 6, 3455-3460
46. Liu, Y.; Li, Dan.; Park, C.-M. Angew. Chem., Int. Ed. 2011, 50, 7333-7336
47. Ruan, J.; Iggo, J. A.; Berry, N. G.; Xiao, J. J. Am. Chem. Soc. 2010, 132, 16689-16699
48. Hyder, Z.; Ruan, J.; Xiao, J. Chem.-Eur. J. 2008, 14, 5555-5566
49. Mo, J.; Xiao, J. Angew. Chem., Int. Ed. 2006, 45, 4152-4157
50. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751-760
51. Ozawa, F.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188-4196
52. Lafrance, M.; Lapointe, D.; Fagnou, K. Tetrahedron 2008, 64, 6015-60220
53. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570-14571
54. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496-16497
55. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345
56. For one recent example, see: Kim, I.-H.; Nishi, K.; Tsai, H.-J.; Bradford, T.; Koda, Y.; Watanabe, T.; Morisseau, C.; Blanchfield, J.; Toth, I.; Hammock, D. D. Bioorg. Med. Chem. 2007, 15, 312-323
57. Kumagai, T.; Tokida, A.; Kidoura, K.; Seshimoto, O.; Mukai, T. Tetrahedron Lett. 1982, 23, 873-876