Zinc-Catalyzed Synthesis of Allylsilanes via Si–H Bond Insertion of Vinyl Carbenoids Generated from Cyclopropenes

Abstract

Allylsilanes have long been recognized as valuable building blocks for organic synthesis. A zinc‐catalyzed reaction of cyclopropenes and hydrosilanes provides a convenient route to these versatile unsaturated organosilanes. In this transformation, ZnBr2 serves as an efficient catalyst, allowing the generation of a zinc vinyl carbenoid intermediate, which is subsequently involved in a Si−H bond insertion. The process shows broad scope, and is amenable to substituted and functionalized cyclopropenes or the functionalization of polysiloxanes. Moreover, zinc‐catalyzed carbene insertion into a Ge−H bond is reported for the first time.