Selective reduction of carboxylic acids to aldehydes by a ruthenium-catalyzed reaction with 1,2-bis(dimethylsilyl)benzene

Chemistry Letters

Volumn 41, Issue 3, 2012, Pages 229-231

  Miyamoto, Konoka ^a   Motoyama, Yukihiro ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84857283138     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2012.229     Document Type: Article

References (26)

1. a) M.B.Smith, J. March, March's Advanced Organic Chemitry: Reactions, Mechanisms, and Structure, 6th ed., Wiley-Interscience, New York, 2007.
2. b) J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed., Wiley, New York, 1997.
3. c) H. C. Brown, S. Krishnamurthy, Tetrahedron 1979, 35, 567.
4. d) E. R. Burkhardt, K. Matos, Chem. Rev. 2006, 106, 2617.
5. A recent typical example: S. Hanessian, S. Guesné, E. Chénard, Org. Lett. 2010, 12, 1816.
6. See, these representative papers and references cited therein: a) P. Four, F. Guibe, J. Org. Chem. 1981, 46, 4439.
7. b) K. Nagayama, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 2001, 74, 1803.
8. c) C. O. Kangani, D. E. Kelley, B. W. Day, Tetrahedron Lett. 2006, 47, 6289.
9. H. C. Brown, J. S. Cha, B. Nazer, N. M. Yoon, J. Am. Chem. Soc. 1984, 106, 8001.
10. J. S. Cha, S. H. Jang, J. H. Park, S. K. Lee, C.-S. Lee, Y. R. Lee, Bull. Korean Chem. Soc. 2003, 24, 9.
11. F. Sato, T. Jinbo, M. Sato, Synthesis 1981, 871.
12. R. J. P. Corriu, G. F. Lanneau, M. Perrot, Tetrahedron Lett. 1987, 28, 3941.
13. For general reviews on the catalytic hydrosilylation: a) I. Ojima, in The Chemistry of Organic Silicon Compounds, ed. by S. Patai, Z. Z. Rappoport, John Wiley & Sons, New York, 1989.
14. b) Comprehensive Handbook on Hydrosilylation, ed. by B. Marciniec, Pergamon, Oxford, 1992.
15. c) Hydrosilylation: A Comprehensive Review on Recent Advances in Advances in Silicon Science, ed. by B. Marciniec, Springer-Verlag, Oxford, 2009, Vol. 1. doi:10.1007/978-1-4020-8172-9.
16. d) D. Addis, S. Das, K. Junge, M. Beller, Angew. Chem., Int. Ed. 2011, 50, 6004.
17. a) H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics 2000, 19, 3579.
18. b) K. Matsubara, T. Iura, T. Maki, H. Nagashima, J. Org. Chem. 2002, 67, 4985.
19. c) Y. Motoyama, K. Mitsui, T. Ishida, H. Nagashima, J. Am. Chem. Soc. 2005, 127, 13150.
20. d) H. Sasakuma, Y. Motoyama, H. Nagashima, Chem. Commun. 2007, 4916.
21. Rate acceleration by proximate SiH groups: a) Rh: H. Nagashima, K. Tatebe, T. Ishibashi, A. Nakaoka, J. Sakakibara, K. Itoh, Organometallics 1995, 14, 2868.
22. c) Pt: S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 15032.
23. d) Ir: Y. Motoyama,M. Aoki, N. Takaoka, R. Aoto, H. Nagashima, Chem. Commun. 2009, 1574.
24. a) H. Nagashima, K. Tatebe, K. Itoh, J. Chem. Soc., Perkin Trans. 1 1989, 1707.
25. b) Y. Sunada, Y. Fujimura, H. Nagashima, Organometallics 2008, 27, 3502.
26. c) R. J. P. Corriu, J. J. E. Moreau, M. Pataud-Sat, J. Organomet. Chem. 1982, 228, 301.