Ir-Catalyzed Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes: A Combined Experimental and Computational Study

J Org Chem. 2016 Aug 5;81(15):6157-64. doi: 10.1021/acs.joc.6b00854. Epub 2016 Jun 7.

Abstract

Iridium complexes are known catalysts for a range of silylation reactions. However, the exploitation for selective hydrosilylation of unsymmetrical internal alkynes has been limitedly known. Described here is a new example of this type. Specifically, [(cod)IrCl]2 catalyzes the efficient and mild hydrosilylation of thioalkynes by various silanes with excellent regio- and stereoselectivity. DFT studies suggested a new mechanism involving Ir(I) hydride as the key intermediate.

Publication types

  • Research Support, Non-U.S. Gov't