A catalytic approach for the functionalization of C(sp3)-H Bonds

Angewandte Chemie - International Edition

Volumn 45, Issue 11, 2006, Pages 1683-1684

  Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,5 hydride shift; C H activation; Catalysis; Lewis acids

Indexed keywords

CATALYSIS; HYDROGEN BONDS; REACTION KINETICS; TRANSITION METALS;

1,5-HYDRIDE SHIFT; C-H ACTIVATION; FUNCTIONALIZATION; LEWIS ACIDS;

INORGANIC ACIDS;

EID: 33746302757     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503866     Document Type: Short Survey

References (44)

1. Recent reviews: a) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077;
2. b) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731.
3. a) N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882;
4. b) N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10935.
5. a) B. D. Dangel, J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2001, 123, 8149;
6. b) B. Sezen, R. Franz, D. Sames, J. Am. Chem. Soc. 2002, 124, 13372;
7. c) B. DeBoef, S. J. Pastine, D. Sames, J. Am. Chem. Soc. 2004, 126, 6556;
8. d) B. Sezen, D. Sames, J. Am. Chem. Soc. 2005, 127, 5284.
9. a) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968;
10. b) Z. Li, C-J. Li, J. Am. Chem. Soc. 2005, 127, 3673;
11. c) Z. Li, C-J. Li, Org. Lett. 2004, 6, 4997;
12. d) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810.
13. a) V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154;
14. b) D. Shabashov, O. Daugulis, Org. Lett. 2005, 7, 3657.
15. a) S.-I. Murahashi, N. Komiya, H. Terai, Angew. Chem. 2005, 117, 7091;
16. Angew. Chem. Int. Ed. 2005, 44, 6931;
17. b) S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15312.
18. a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
19. b) S. Shimada, A. S. Batsanov, J. A. K. Howard, T. B. Marder, Angew. Chem. 2001, 113, 2226;
20. Angew. Chem. Int. Ed. 2001, 40, 2168.
21. F. Kakiuchi, K. Tsuchiya, M. Matsumoto, E. Mizushima, N. Chatani, J. Am. Chem. Soc. 2004, 126, 12792.
22. a) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
23. b) L. V. Desai, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 9542;
24. c) A. R. Dick, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 2301;
25. d) R. Giri, X. Chen, J.-Q. Yu, Angew. Chem. 2005, 117, 2150;
26. Angew. Chem. Int. Ed. 2005, 44, 2112;
27. e) R. Giri, J. Riang, J.-G. Lei, J.-J. Li, D.-H. Wang, X. Chen, I. C. Naggar, C. Guo, B. M. Foxman, J.-Q. Yu, Angew. Chem. 2005, 117, 7586;
28. Angew. Chem. Int. Ed. 2005, 44, 7420.
29. a) J. L. Liang, S.-X. Yuan, J.-S. Huang, W.-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615;
30. Angew. Chem. Int. Ed. 2002, 41, 3465;
31. b) C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618;
32. Angew. Chem. Int. Ed. 2001, 40, 598;
33. c) P. M. When, J. Du Bois, J. Am. Chem. Soc. 2002, 124, 12950;
34. d) P. M. When, J. Lee, J. Du Bois, Org. Lett. 2003, 5, 4823;
35. e) J. J. Fleming, K. W. Fiori, J. Du Bois, J. Am. Chem. Soc. 2003, 125, 2028;
36. f) K. W. Fiori, J. J. Fleming, J. Du Bois, Angew. Chem. 2004, 116, 4449;
37. Angew. Chem. Int. Ed. 2004, 43, 4349;
38. g) C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378.
39. a) A. D. Ryabov, Chem. Rev. 1990, 90, 403;
40. b) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
41. S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180.
42. [2,4,6]
43. M. Noguchi, H. Yamada, T. Sunagawa, J. Chem. Soc. Perkin Trans. 1 1998, 3327; see also references cited in reference [12].
44. During the preparation of this manuscript, another application of the methodology was reported: S. J. Pastine, D. Sames, Org. Lett. 2005, 7, 5429.