A palladium-catalyzed route for α-alkylation of ketones by primary alcohols

Journal of Molecular Catalysis A: Chemical

Volumn 240, Issue 1-2, 2005, Pages 55-60

  Cho, Chan Sik ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Alkylation; Hydrogen acceptor; Ketones; Palladium catalyst; Primary alcohols

Indexed keywords

ALKYLATION; CATALYSIS; CONDENSATION; HYDROGEN; OXIDATION; PALLADIUM;

HYDROGEN ACCEPTOR; PALLADIUM CATALYSTS; PRIMARY ALCOHOLS;

KETONES;

EID: 24144462600     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.06.043     Document Type: Article

References (40)

1. D. Caine B.M. Trost I. Fleming Comprehensive Organic Synthesis vol. 3 1991 Pergamon Press Oxford 1 63
2. J. d'Angelo Tetrahedron 32 1976 2979
3. Y. Inoue, M. Toyofuku, M. Taguchi, S. Okada, and H. Hashimoto Bull. Chem. Soc. Jpn. 59 1986 885 For transition metal-catalyzed α-alkylation of, ketones
4. N. Yoshikawa, Y.M.A. Yamada, J. Das, H. Sasai, and M. Shibasaki J. Am. Chem. Soc. 121 1999 4168
5. D.H. Camacho, I. Nakamura, B.H. Oh, S. Saito, and Y. Yamamoto Tetrahedron Lett. 43 2002 2903
6. C.S. Cho, B.T. Kim, T.-J. Kim, and S.C. Shim Tetrahedron Lett. 43 2002 7987
7. C.S. Cho, B.T. Kim, T.-J. Kim, and S.C. Shim J. Org. Chem. 66 2001 9020
8. C.S. Cho, B.T. Kim, H.-S. Kim, T.-J. Kim, and S.C. Shim Organometallics 22 2003 3608 It was also disclosed that aryl(methyl) and alkyl(methyl) carbinols were found to couple with primary alcohols 2 in the presence of a ruthenium catalyst along with sacrificial hydrogen acceptor to give secondary alcohols 4
9. C.S. Cho, B.T. Kim, T.-J. Kim, and S.C. Shim Chem. Commun. 2001 2576 This methodology could also be successfully applied to modified Friedlaender quinoline synthesis by the ruthenium-catalyzed oxidative cyclization of 2-aminobenzyl alcohol with ketones and secondary alcohols
10. C.S. Cho, B.T. Kim, H.-J. Choi, T.-J. Kim, and S.C. Shim Tetrahedron 59 2003 7997
11. K. Taguchi, H. Nakagawa, T. Hirabayashi, S. Sakaguchi, and Y. Ishii J. Am. Chem. Soc. 126 2004 72
12. C.S. Cho, D.K. Lim, N.H. Heo, T.-J. Kim, and S.C. Shim Chem. Commun. 2004 104 For our recent report on palladium catalysis
13. C.S. Cho, D.K. Lim, J.Q. Zhang, T.-J. Kim, and S.C. Shim Tetrahedron Lett. 45 2004 5653
14. L.J. Goossen, and K. Ghosh Eur. J. Org. Chem. 19 2002 3254
15. C. Grison, A. Thomas, F. Coutrot, and P. Coutrot Tetrahedron 59 2003 2101
16. A.E. Jensen, and P. Knochel J. Org. Chem. 67 2002 79
17. D.F. Taber, S. Kong, and S.C. Malcolm J. Org. Chem. 63 1998 7953
18. N. Yoneda, Y. Takahashi, and A. Suzuki Chem. Lett. 1978 231
19. M. Piber, A.E. Jensen, M. Rottländer, and P. Knochel Org. Lett. 1 1999 1323
20. B.A. Kulkarni, and A. Ganesan J. Comb. Chem. 1 1999 373
21. J.F. Hayes, M. Shipman, and H. Twin J. Org. Chem. 67 2002 935
22. R.K. Dieter, R.R. Sharma, H. Yu, and V.K. Gore Tetrahedron 59 2003 1083
23. Y. Hoshino, H. Tanaka, and N. Takeno Bull. Chem. Soc. Jpn. 71 1998 2923
24. G. Zassinovich, G. Mestroni, and S. Gladiali Chem. Rev. 92 1992 1051 For recent reviews on transition metal-catalyzed transfer hydrogenation, see
25. J.-E. Bäckvall, R.L. Chowdhury, U. Karlsson, and G. Wang A.F. Williams C. Floriani A.E. Merbach Perspectives in Coordination Chemistry 1992 VCH Publishers New York 463 486
26. R. Noyori, and S. Hashiguchi Acc. Chem. Res. 30 1997 97
27. T. Naota, H. Takaya, and S.-I. Murahashi Chem. Rev. 98 1998 2599
28. M. Palmer, and M. Wills Tetrahedron: Asymmetry 10 1999 2045
29. M. Palucki, and S.L. Buchwald J. Am. Chem. Soc. 119 1997 11108
30. B.C. Hamann, and J.F. Hartwig J. Am. Chem. Soc. 119 1997 12382
31. C.S. Cho, B.T. Kim, M.J. Lee, T.-J. Kim, and S.C. Shim Angew. Chem., Int. Ed. 40 2001 958
32. Y. Tamaru, Y. Yamamoto, Y. Yamada, and Z. Yoshida Tetrahedron Lett. 1979 1401
33. Y. Tamaru, K. Inoue, Y. Yamada, and Z. Yoshida Tetrahedron Lett. 22 1981 1801
34. B.M. Choudary, N.P. Reddy, M.L. Kantam, and Z. Jamil Tetrahedron Lett. 26 1985 6257
35. Y. Aoyagi, T. Mizusaki, and A. Ohta Tetrahedron Lett. 37 1996 9203
36. H. Nagashima, and J. Tsuji Chem. Lett. 1981 1171
37. Y.R. Santosh Laxmi, and J.-E. Bäckvall Chem. Commun. 2000 611 For transition metal-catalyzed transfer hydrogenation of ketones by alcohols
38. Y. Sasson, and J. Blum Tetrahedron Lett. 1971 2167 Carbon-carbon double bond of α,β-unsaturated carbonyl compounds as a hydrogen acceptor for ruthenium-catalyzed oxidation of alcohols to ketones
39. S.L. Regen, and G.M. Whitesides J. Org. Chem. 37 1972 1832
40. Y. Sasson, and G.L. Rempel Tetrahedron Lett. 1974 4133