Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates

Angewandte Chemie - International Edition

Volumn 50, Issue 44, 2011, Pages 10402-10405

  Qian, Xin ^a   Auffrant, Audrey ^a   Felouat, Abdellah ^a   Gosmini, Corinne ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

alkyl halides; allylation; C C coupling; cobalt; homogeneous catalysis

Indexed keywords

ALKYL HALIDES; C-C COUPLING; EFFICIENT METHOD; HOMOGENEOUS CATALYSIS;

ALLYLATION; BROMINE COMPOUNDS; CARBONATES; CATALYSIS; FUNCTIONAL GROUPS; REACTION KINETICS;

COBALT;

EID: 80054968441     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104390     Document Type: Article

References (46)

1. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943
2. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303
3. Angew. Chem. Int. Ed. 2008, 47, 258-297
4. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417-1492.
5. B. M. Trost, M. H. Hung, J. Am. Chem. Soc. 1983, 105, 7757-7759
6. B. M. Trost, G. B. Tometzki, M. H. Hung, J. Am. Chem. Soc. 1987, 109, 2176-2177
7. G. C. Lloyd-Jones, A. Pfaltz, Angew. Chem. 1995, 107, 534-536
8. Angew. Chem. Int. Ed. Engl. 1995, 34, 462-464
9. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2007, 129, 14548-14549.
10. B. Bartels, G. Helmchen, Chem. Commun. 1999, 741-742
11. R. Takeuchi, N. Shiga, Org. Lett. 1999, 1, 265-267.
12. Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405-10406
13. K. Onitsuka, Y. Matsushima, S. Takahashi, Organometallics 2005, 24, 6472-6474.
14. T. Hayashi, A. Okada, T. Suzuka, M. Kawatsura, Org. Lett. 2003, 5, 1713-1715.
15. A. J. Blacker, M. L. Clark, M. S. Loft, J. M. J. Williams, Chem. Commun. 1999, 913-914.
16. B. Plietker, Angew. Chem. 2006, 118, 1497-1501
17. Angew. Chem. Int. Ed. 2006, 45, 1469-1473
18. M. Holzwarth, A. Dieskau, M. Tabassam, B. Plietker, Angew. Chem. 2009, 121, 7387-7391
19. Angew. Chem. Int. Ed. 2009, 48, 7251-7255.
20. N. Nomura, T. V. Rajan Babu, Tetrahedron Lett. 1997, 38, 1713-1716
21. S. Son, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 2756-2757.
22. C. Kishan Reddy, P. Knochel, Angew. Chem. 1996, 108, 1812-1813
23. Angew. Chem. Int. Ed. Engl. 1996, 35, 1700-1701
24. T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. 2002, 114, 4311-4313
25. Angew. Chem. Int. Ed. 2002, 41, 4137-4139
26. H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10, 5640-5648.
27. C. A. Falciola, K. Tissot-Croset, A. Alexakis, Angew. Chem. 2006, 118, 6141-6144
28. Angew. Chem. Int. Ed. 2006, 45, 5995-5998
29. E. Erdik, M. Koçoǧlu, Tetrahedron Lett. 2007, 48, 4211-4214
30. M. Sai, H. Yorimitsu, K. Oshima, Bull. Chem. Soc. Jpn. 2009, 82, 1194-1196
31. A. M. Lauer, F. Mahmud, J. Wu, J. Am. Chem. Soc. 2011, 133, 9119-9123.
32. M. Amatore, C. Gosmini, Synlett 2009, 1073-1076
33. A. Moncomble, P. L. Floch, C. Gosmini, Chem. Eur. J. 2009, 15, 4770-4774
34. M. Amatore, C. Gosmini, Chem. Eur. J. 2010, 16, 5848-5852
35. D. A. Everson, R. Shrestha, D. J. Weix, J. Am. Chem. Soc. 2010, 132, 920-921
36. M. R. Prinsell, D. A. Everson, D. J. Weix, Chem. Commun. 2010, 46, 5743-5745
37. X. Yu, T. Yang, S. Wang, H. Xu, H. Gong, Org. Lett. 2011, 13, 2138-2141; for stoichiometric reactions, see
38. D. C. Billington, Chem. Soc. Rev. 1985, 14, 93-120
39. M. Durandetti, J. Y. Nedelec, J. Périchon, J. Org. Chem. 1996, 61, 1748-1755.
40. P. Gomes, C. Gosmini, J. Périchon, Org. Lett. 2003, 5, 1043-1045.
41. C. Gosmini, A. Moncomble, Isr. J. Chem. 2010, 50, 568-576.
42. A. Joshi-Pangu, C.-Y. Wang, M. R. Biscoe, J. Am. Chem. Soc. 2011, 133, 8478-8481
43. C. Lohre, T. Dröge, C. Wang, F. Glorius, Chem. Eur. J. 2011, 17, 6052-6055.
44. L. Hintermann, L. Xiao, A. Labonne, Angew. Chem. 2008, 120, 8370-8374
45. Angew. Chem. Int. Ed. 2008, 47, 8246-8250.
46. M. Durandetti, C. Gosmini, J. Périchon, Tetrahedron 2007, 63, 1146-1153.