An Efficient Synthesis of Unsymmetrical 1,1-Bis(silyl)ethenes

Abstract

A new convenient and effective method for the synthesis of unsymmetrical 1,1-bis(silyl)ethenes is described. The synthetic methodology involves selective silylative coupling cyclization of N-methyl-N-(dimethylvinylsilyl)-2-(dimethylvinylsilyloxy)ethan­amine catalyzed by a ruthenium hydride complex and subsequent one-pot reaction of the cyclic bis(silyl)derivative with Grignard reagents followed by alcoholysis. As a result, a variety of 1,1-bis(silyl)ethenes containing different substituents at the silicon atoms were produced in regiocontrolled manner with considerably high efficiency.

Key words

vinylsilanes - silylative coupling - amino alcohol - Grignard reactions - organometallic reagents

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