Rhodium-catalyzed alkenylation of nitriles via silicon-assisted C-CN bond cleavage

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1864-1867

  Kita, Yusuke ^a   Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77951185846     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100481h     Document Type: Article

References (56)

1. For reviews of the Mizoroki-Heck reaction, see: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
2. Whitcombe, N. J.; Hii, K. K. M.; Gibson, S. E. Tetrahedron 2001, 57, 7449
3. Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007, 5, 31
4. The Mizoroki-Heck Reactione; Oestreich, M., Ed.; Wiley-VCH: Weinheim, 2009.
5. Selected recent examples; aroyl chloride
6. Sugihara, T.; Satoh, T.; Miura, M. Tetrahedron Lett. 2005, 46, 8269. Diazonium salt:
7. Kikukawa, K.; Ikenaga, K.; Kono, K.; Toritani, K.; Wada, F.; Matsuda, T. J. Organomet. Chem. 1984, 270, 277
8. Arylsulfonyl chloride: Dubbaka, S. R.; Vogel, P. Chem. - Eur. J. 2005, 11, 2633
9. N -nitroso- N -arylacetamide: Kikukawa, K.; Naritomi, M.; He, G. X.; Wada, F.; Matsuda, T. J. Org. Chem. 1985, 50, 299. Aryl phoshonium salt:
10. Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 6166. Hypervalent iodo compound:
11. Aydin, J.; Larsson, J. M.; Selander, N.; Szabo, K. J. Org. Lett. 2009, 11, 2852-2854
12. Selected recent examples; M = B
13. Xiong, D.-C.; Zhang, L.-H.; Ye, X.-S. Org. Lett. 2009, 11, 170 M = Sn
14. Parrish, J. P.; Jung, Y. C.; Shin, S. I.; Jung, K. W. J. Org. Chem. 2002, 67, 7127 M = Si:
15. 2
16. Inoue, A.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 1484 M = Bi
17. Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910 M = Sb
18. Matoba, K.; Motofusa, S.-i.; Sik Cho, C.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1999, 574, 3
19. A review
20. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633 A recent report:
21. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
22. Gooßen, L. J.; Paetzold, J.; Winkel, L. Synlett 2002, 1721
23. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
24. Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433
25. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
26. Hu, P.; Kan, J.; Su, W.; Hong, M. Org. Lett. 2009, 11, 2341
27. Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152
28. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982
29. Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174
30. For reviews on this topic, see
31. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
32. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
33. Miura, T.; Murakami, M. Chem. Commun. 2007, 217
34. Nakao, Y.; Yada, A.; Satoh, J.; Ebata, S.; Oda, S.; Hiyama, T. Chem. Lett. 2006, 35, 790
35. Tobisu, M.; Hyodo, I.; Onoe, M.; Chatani, N. Chem. Commun. 2008, 6013
36. 3 (42%, 42%), bipyridine (25%, 10%), IPr (55%, 28%).
37. For the results using other vinylsilanes, see the Supporting Information.
38. Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2002, 124, 4192
39. Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808
40. Nakazawa, H.; Kawasaki, T.; Miyoshi, K.; Suresh, C. H.; Koga, N. Organometallics 2003, 23, 117
41. Itazaki, M.; Nakazawa, H. Chem. Lett. 2005, 34, 1054
42. Nakazawa, H.; Kamata, K.; Itazaki, M. Chem. Commun. 2005, 4004
43. Nakazawa, H.; Itazaki, M.; Kamata, K.; Ueda, K. Chem. Asian J. 2007, 2, 882
44. Ochiai, M.; Hashimoto, H.; Tobita, H. Angew. Chem., Int. Ed. 2007, 46, 8192
45. 3, which also serves as a catalytically active species. If this mechanism is operative, the catalytic reaction should work even with a catalytic amount of disilane. However, the yield of the alkenylated product significantly decreased as the amount of disilane was reduced.
46. Electrophilic substitution
47. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57 Addition to aldehydes:
48. Aikawa, K.; Hioki, Y.-t.; Mikami, K. J. Am. Chem. Soc. 2009, 131, 13922 and references therein. Coupling with alcohol:
49. Nishimoto, Y.; Kajioka, M.; Saito, T.; Yasuda, M.; Baba, A. Chem. Commun. 2008, 6396
50. Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2009, 48, 3565
51. Wang, C.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 5240
52. For iterative synthesis of oligo(phenylenevinylene)s, see
53. Iwadate, N.; Suginome, M. Org. Lett. 2009, 11, 1899
54. Jørgensen, M.; Krebs, F. C. J. Org. Chem. 2005, 70, 6004
55. For the utility of oligo(phenylenevinylene)s in materials, see
56. Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644