Ruthenium-catalyzed propargylic reduction of propargylic alcohols with silanes

Angewandte Chemie - International Edition

Volumn 45, Issue 29, 2006, Pages 4835-4839

  Nishibayashi, Yoshiaki ^a   Shinoda, Akira ^b   Miyake, Yoshihiro ^a   Matsuzawa, Hiroshi ^a   Sato, Mitsunobu ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b KOGAKUIN UNIVERSITY   (Japan)

Author keywords

Homogeneous catalysis; Reduction; Ruthenium; Silanes; Synthetic methods

Indexed keywords

CATALYSIS; CATALYSTS; HYDRIDES; REDUCTION; RUTHENIUM; SILANES;

PROPARGYLIC ALCOHOLS; PROPARGYLIC REDUCTION; SYNTHETIC METHODS;

ALCOHOLS;

EID: 33746807241     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601181     Document Type: Article

References (43)

1. a) I. Ojima, The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989, p. 1479;
2. b) T. Hiyama, T. Kusumoto, Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, UK, 1991, p. 763;
3. c) B. Marciniec, Comprehensive Handbook on Hydrosilylation, Pergamon, Oxford, UK, 1992, p. 130;
4. d) J. A. Reiche, D. H. Bery, Adv. Organomet. Chem. 1998, 43, 197;
5. e) For a recent example, see: B. M. Trost, Z. T. Ball, Synthesis 2005, 853.
6. a) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12 726;
7. b) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2003, 125, 30;
8. c) B. M. Trost, Z. T. Ball, T. Jöge, Angew. Chem. 2003, 115, 3537;
9. Angew. Chem. Int. Ed. 2003, 42, 3415;
10. d) L. W. Chung, Y.-D. Wu, B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2003, 125, 11 578;
11. e) B. M. Trost, Z. T. Ball, K. M. Laemmerhold, J. Am. Chem. Soc. 2005, 127, 10 028;
12. f) B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2005, 127, 17 644.
13. a) K. Itami, K. Mitsudo, A. Nishino, J. Yoshida, J. Org. Chem. 2002, 67, 2645;
14. b) Y. Kawanami, Y. Sonoda, T. Mori, K. Yamamoto, Org. Lett. 2002, 4, 2825;
15. c) A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A. P. Mudalige, H. Kajiro, K. Hirabayashi, Y. Nishihara, T. Hiyama, Organometallics 2004, 23, 1755;
16. d) H. Aneetha, W. Wu, J. G. Verkade, Organometallics 2005, 24, 2590;
17. e) H. Katayama, M. Nagao, T. Nishimura, Y. Matsui, K. Umeda, K. Akamatsu, T. Tsuruoka, H. Nawafune, F. Ozawa, J. Am. Chem. Soc. 2005, 127, 4350;
18. f) M. Nagao, K. Asano, K. Umeda, H. Katayama, F. Ozawa, J. Org. Chem. 2005, 70, 10 511;
19. g) C. Menozzi, P. I. Dalko, J. Cossy, J. Org. Chem. 2005, 70, 10 717;
20. h) G. D. Bo, G. Berthon-Gelloz, B. Tinant, I. E. Markó, Organometallics 2006, 25, 1881.
21. a) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai, S. Uemura, Organometallics 2004, 23, 26;
22. b) Y. Nishibayashi, H. Imajima, G. Onodera, Y. Inada, M. Hidai, S. Uemura, Organometallics 2004, 23, 5100.
23. a) S. C. Ammal, N. Yoshikai, Y. Inada, Y. Nishibayashi, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 9428;
24. b) Y. Inada, Y. Nishibayashi, S. Uemura, Angew. Chem. 2005, 117, 7893;
25. Angew. Chem. Int. Ed. 2005, 44, 7715;
26. c) Y. Inada, M. Yoshikawa, M. D. Milton, Y. Nishibayashi, S. Uemura, Eur. J. Org. Chem. 2006, 881.
27. Re: a) B. D. Sherry, A. T. Radosevich, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 6076;
28. Au: b) M. Georgy, V. Boucard, J.-M. Campagne, J. Am. Chem. Soc. 2005, 127, 14 180.
29. Cu: Y. Imada, M. Yuasa, I. Nakamura, S.-I. Murahashi, J. Org. Chem. 1994, 59, 2282.
30. Ti: R. Mahrwald, S. Quint, Tetrahedron 2000, 56, 7463.
31. Ir: I. Matsuda, K. Komori, K. Itoh, J. Am. Chem. Soc. 2002, 124, 9072.
32. Re: a) M. R. Luzung, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 15 760;
33. b) J. J. Kennedy-Smith, L. A. Young, F.D. Toste, Org. Lett. 2004, 6, 1325;
34. c) R. V. Ohri, A. T. Radosevich, K. J. Hrovat, C. Musich, D. Huang, T. R. Holman, F. D. Toste, Org. Lett. 2005, 7, 2501.
35. G. Onodera, Y. Nishibayashi, S. Uemura, Organometallics 2006, 25, 35.
36. No reaction occurred when 2m, 2q, or 2r was used as a substrate.
37. a) K. M. Nicholas, J. Siegel, J. Am. Chem. Soc. 1985, 107, 4999;
38. b) K. M. Nicholas, Acc. Chem. Res. 1987, 20, 207.
39. M. Yasuda, Y. Onishi, M. Ueba, T. Miyai, A. Baba, J. Org. Chem. 2001, 66, 7741.
40. a) V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919;
41. b) V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179.
42. N. Sakai, M. Hirasawa, T. Konakahara, Tetrahedron Lett. 2005, 46, 6407.
43. Separately, we investigated the reaction of 2 a with a mixture of allyltrimethylsilane and triethylsilane in the presence of 5 mol % of 1c at 80°C for 1 h; only 7a was isolated in 81 % yield.