Synlett
DOI: 10.1055/s-0036-1588441
cluster
© Georg Thieme Verlag Stuttgart · New York

Exhaustive Chemoselective Reduction of Nitriles by Catalytic Hydrosilylation Involving Cooperative Si–H Bond Activation

Simon Wübbolt, Martin Oestreich*
This research was supported by the Deutsche Forschungsgemeinschaft (Oe 249/10-1). M.O. is indebted to the Einstein Foundation (Berlin) for an endowed professorship
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Publication History

Received: 09 March 2017

Accepted after revision: 09 May 2017

Publication Date:
31 May 2017 (eFirst)

Published as part of the Cluster Silicon in Synthesis and Catalysis

Abstract

A chemoselective method for the catalytic hydrosilylation of nitriles to either the imine or amine oxidation level is reported. The chemoselectivity is controlled by the hydrosilane used. The usefulness of the nitrile-to-amine reduction is demonstrated for a diverse set of aromatic and aliphatic nitriles, and the amines are easily isolated after hydrolysis as their hydrochloride salts. This exhaustive nitrile reduction proceeds at room temperature.

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