Synthesis 2004(2): 308-311  
DOI: 10.1055/s-2003-44356
PSP
© Georg Thieme Verlag Stuttgart · New York

Reduction of Carbonyl Function to a Methyl Group

Gan B. Bajracharyaa, Tsutomu Nogamia, Tienan Jina, Kumiko Matsudaa, Vladimir Gevorgyanb, Yoshinori Yamamoto*a
a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Fax: +81(22)2176784; e-Mail: [email protected];
b Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA
Further Information

Publication History

Received 29 September 2003
Publication Date:
03 December 2003 (online)

Abstract

A direct exhaustive reduction of aliphatic carbonyl functions (aldehydes, acyl chlorides, esters and carboxylic acids) to a methyl group by triethylsilane (Et3SiH) in the presence of catalytic amount of tris(pentafluorophenyl)borane [B(C6F5)3] is described. Aromatic carbonyl functions could undergo partial reduction to the corresponding TES-protected benzylic alcohols.

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13

A similar partial reduction of carbonyl functions by using Ph3SiH has been recently reported, see Ref. [10]