Synlett 2008(12): 1915-1916  
DOI: 10.1055/s-2008-1077884
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Trichlorosilane (HSiCl3) - A Cheap and Convenient Reducing Agent

Zhiguo Zhang*
Institut für Organische Chemie, Justus-Liebig-Universität Gießen, Heinrich-Buff-Ring 58, 35392 Gießen, Germany
e-Mail: zhiguo.zhang@org.chemie.uni-giessen.de;
Further Information

Publication History

Publication Date:
11 June 2008 (online)

Introduction

Trichlorosilane (HSiCl3) is a cheap, stable, and commercially available reagent, which has been widely used as stoichiometric reductant. In general, activators are necessary for HSiCl3 to reduce efficiently C=C, C=O, C=N, and P=O functionalities. The currently most successful methodologies are based on transition-metal-centered catalyzed hydrosilylation; however, recent advances in the field of organocatalysis have also provided a series of small organic molecules as efficient alternative catalysts for asymmetric reductions of ketones or imines with HSiCl3. In this paper, reductions using HSiCl3 are summarized.

A number of methods are available for the preparation of trichlorosilane in the laboratory, for example, by the reaction of dry HCl gas with silicon (Scheme  [¹] ) [¹] or with metallic silicides. [²] The title compound is also an abundant byproduct of the industrial Rochow process. [³]

Scheme 1

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