Indium triiodide catalyzed reductive functionalization of amides via the single-stage treatment of hydrosilanes and organosilicon nucleophiles

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3452-3455

  Inamoto, Yoshihiro ^a   Kaga, Yuta ^a   Nishimoto, Yoshihiro ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880013939     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4015317     Document Type: Article

References (44)

1. Cope, A. C.; Ciganek, E. Org. Synth. 1963, 4, 339-342
2. Seyden-Penne, J. In Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2 nd ed.; Wiley-VCH: New York, 1997; p 1.
3. Kuwano, R.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 1017-1020
4. Motoyama, Y.; Mitsui, K.; Ishida, T.; Nagashima, H. J. Am. Chem. Soc. 2005, 127, 13150-13151
5. Hanada, S.; Tsutsumi, E.; Motoyama, Y.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 15032-15040
6. Sunada, Y.; Kawakami, H.; Imaoka, T.; Motoyama, Y.; Nagashima, H. Angew. Chem., Int. Ed. 2009, 48, 9511-9514
7. Sakai, N.; Fujii, K.; Konakahara, T. Tetrahedron Lett. 2008, 49, 6873-6875
8. Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 9507-9510
9. Das, S.; Addis, D.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2010, 132, 1770-1771
10. Das, S.; Wendt, B.; Möller, K.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2012, 51, 1662-1666
11. Park, S.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 640-653
12. Cheng, C.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 11304-11307
13. Addis, D.; Das, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 6004-6011
14. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 1719-1722
15. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Am. Chem. Soc. 1985, 107, 5534-5535
16. Vincent, G.; Guillot, R.; Kouklovsky, C. Angew. Chem., Int. Ed. 2011, 50, 1350-1353
17. Hwang, Y. C.; Chu, M.; Flower, F. W. J. Org. Chem. 1985, 50, 3885-3890
18. Overman, L. E.; Lesuisse, D.; Hashimoto, M. J. Am. Chem. Soc. 1983, 105, 5373-5379
19. Tschinkl, M.; Schier, A.; Riede, J.; Gabbaï, F. P. Angew. Chem., Int. Ed. 1999, 38, 3545-3547
20. Larouche-Gauthier, R.; Bélanger, G. Org. Lett. 2008, 10, 4501-4504
21. Bélanger, G.; O'Brien, G.; Larouche-Gauthier, R. Org. Lett. 2011, 13, 4268-4271
22. Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew, Chem., Int. Ed. 2010, 49, 3037-3040
23. Xiao, K.-J.; Wang, Y.; Ye, K.-Y.; Huang, P.-Q. Chem.-Eur. J. 2010, 16, 12792-12796
24. Xiao, K.-J.; Wang, A.-E.; Huang, P.-Q. Angew. Chem., Int. Ed. 2012, 51, 8314-8317
25. Huo, H.-H.; Zhang, H.-K.; Xia, X.-E.; Huang, P.-Q. Org. Lett. 2012, 14, 4834-4937
26. Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 18-19
27. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817-12819
28. Shirokake, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2010, 49, 6369-6372
29. Oda, Y.; Sato, T.; Chida, N. Org. Lett. 2012, 14, 950-953
30. Yanagita, Y.; Nakamura, H.; Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Chem.-Eur. J. 2013, 19, 678-684
31. Seebach, D. Angew. Chem., Int. Ed. 2011, 50, 96-101
32. Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123, 9706-9707
33. Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469-1471
34. Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968-5969
35. Murai, T.; Asai, F. J. Am. Chem. Soc. 2007, 129, 780-781
36. Agosti, A.; Britto, S.; Renaud, P. Org. Lett. 2008, 10, 1417-1420
37. Murai, T.; Mutoh, Y. Chem. Lett. 2012, 41, 2-8
38. Nishimoto, Y.; Inamoto, Y.; Saito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2010, 3382-3386
39. Inamoto, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2012, 14, 1168-1171
40. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353
41. For the reactivity order of organosilicon nucleophiles, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77
42. Shono, T.; Tsubata, K.; Okinaga, N. J. Org. Chem. 1984, 49, 1056-1059
43. Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761-1764
44. Our previous report, which conducted the indium(III)-catalyzed allylation of imines, shows that the introduction of a tosyl group gave good results; see: Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Tetrahedron 2002, 58, 8227-8235 (Japan)