Me2s-induced highly selective reduction of aldehydes in the presence of ketones involving aldehyde-selective rate enhancement: A triruthenium cluster-catalyzed hydrosilylation

Chemistry Letters

Volumn 43, Issue 12, 2014, Pages 1829-1831

  Yumino, Shohei ^a   Hashimoto, Toru ^a   Tahara, Atsushi ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84918507450     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.140731     Document Type: Article

References (34)

1. March's Advanced Organic Chemistry, 6th ed., ed. by M. B. Smith, J. March, Wiley Interscience, New Jersey, 2007. doi:10.1002/0470084960.
2. Reduction by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed., ed. by J. Seyden-Penne, Wiley-VCH, 1997.
3. H. C. Brown, S. Krishnamurthy, Tetrahedron 1979, 35, 567.
4. D. E. Ward, C. K. Rhee, Can. J. Chem. 1989, 67, 1206.
5. Y. Kuroiwa, S. Matsumura, K. Toshima, Synlett 2008, 2523.
6. B. C. Ranu, Synlett 1993, 885.
7. B. Zeynizadeh, Bull. Chem. Soc. Jpn. 2003, 76, 317.
8. S. Krishnamurthy, J. Org. Chem. 1981, 46, 4628.
9. H. C. Brown, S. U. Kulkarni, J. Org. Chem. 1977, 42, 4169.
10. Hydrosilylation, ed. by B. Marciniec, Springer, 2009. doi:10.1007/978-1-4020-8172-9.
11. Comprehensive Handbook on Hydrosilylation, ed. by B. Marciniec, Pergamon Press, Oxford, 1992.
12. I. Ojima, in The Chemistry of Organic Silicon Compounds, ed. by S. Patai, Z. Rappoport, Wiley, Chichester, 1989, Vol. 1, Chap. 25, pp. 14791526. doi:10.1002/0470025107.ch25.
13. I. Ojima, Z. Li, J. Zhu, in The Chemistry of Organic Silicon Compounds, ed. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, 1998, Vol. 2, Chap. 29, pp. 16871792. doi:10.1002/0470857250.ch29.
14. Au: H. Ito, T. Yajima, J. Tateiwa, A. Hosomi, Chem. Commun. 2000, 981.
15. Cu: B. H. Lipshutz, W. Chrisman, K. Noson, J. Organomet. Chem. 2001, 624, 367.
16. Ag: B. M. Wile, M. Stradiotto, Chem. Commun. 2006, 4104.
17. Au, Ag, and Cu: S. Díez-González, S. P. Nolan, Acc. Chem. Res. 2008, 41, 349.
18. Ru: Y. Do, J. Han, Y. H. Rhee, J. Park, Adv. Synth. Catal. 2011, 353, 3363.
19. Fe: N. S. Shaikh, K. Junge, M. Beller, Org. Lett. 2007, 9, 5429.
20. Base: R. J. P. Corriu, R. Perz, C. Reye, Tetrahedron 1983, 39, 999.
21. Base and F: C. Chuit, R. J. P. Corriu, R. Perz, C. Reyé, Synthesis 1982, 981.
22. Selective examples for other reduction methods: a) J. Tsuji, H. Suzuki, Chem. Lett. 1977, 1085.
23. G. Wienhöfer, F. A. Westerhaus, K. Junge, R. Ludwig, M. Beller, Chem.-Eur. J. 2013, 19, 7701.
24. J. R. Miecznikowski, R. H. Crabtree, Polyhedron 2004, 23, 2857.
25. J. Lee, T. Ryu, S. Park, P. H. Lee, J. Org. Chem. 2012, 77, 4821.
26. H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics 2000, 19, 3579.
27. K. Matsubara, T. Iura, T. Maki, H. Nagashima, J. Org. Chem. 2002, 67, 4985.
28. Y. Motoyama, K. Mitsui, T. Ishida, H. Nagashima, J. Am. Chem. Soc. 2005, 127, 13150.
29. H. Sasakuma, Y. Motoyama, H. Nagashima, Chem. Commun. 2007, 4916.
30. K. Miyamoto, Y. Motoyama, H. Nagashima, Chem. Lett. 2012, 41, 229.
31. E. P. L. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413.
32. 3SiH and a catalytic amount of 1. See: a) H. Nagashima, C. Itonaga, J. Yasuhara, Y. Motoyama, K. Matsubara, Organometallics 2004, 23, 5779.
33. N. Harada, J. Yasuhara, Y. Motoyama, O. Fujimura, T. Tsuji, T. Takahashi, Y. Takahashi, H. Nagashima, Bull. Chem. Soc. Jpn. 2011, 84, 26.
34. For a related compound of D' was investigated: N. J. Leonard, T. W. Milligan, T. L. Brown, J. Am. Chem. Soc. 1960, 82, 4075.