Reduction of Carbonyl Function to a Methyl Group

Gan B. Bajracharya; Tsutomu Nogami; Tienan Jin; Kumiko Matsuda; Vladimir Gevorgyan; Yoshinori Yamamoto

doi:10.1055/s-2003-44356

PSP

Reduction of Carbonyl Function to a Methyl Group

Gan B. Bajracharya^a, Tsutomu Nogami^a, Tienan Jin^a, Kumiko Matsuda^a, Vladimir Gevorgyan^b, Yoshinori Yamamoto*^a
^a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Fax: +81(22)2176784; e-Mail: yoshi@yamamoto1.chem.tohoku.ac.jp;
^b Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA

Abstract

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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.

Key words

reductions - aldehydes - acyl chlorides - esters - carboxylic acids

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References

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