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Synlett 2017; 28(18): 2411-2414
DOI: 10.1055/s-0036-1588441
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© Georg Thieme Verlag Stuttgart · New York

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

Simon Wübbolt 
Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany   eMail: martin.oestreich@tu-berlin.de
,
Martin Oestreich  *
Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany   eMail: martin.oestreich@tu-berlin.de
› InstitutsangabenThis 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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Publikationsverlauf

Received: 09. März 2017

Accepted after revision: 09. Mai 2017

Publikationsdatum:
31. Mai 2017 (online)

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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.

Key words

chemoselectivity - cooperativity - hydrosilylation - reduction - silicon

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588441.
  • Supporting Information
 

  • References and Notes

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