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Zinc‐Catalyzed Synthesis of Allylsilanes by Si−H Bond Insertion of Vinyl Carbenoids Generated from Cyclopropenes
Author(s) -
Mata Sergio,
López Luis A.,
Vicente Rubén
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201703319
Subject(s) - carbenoid , zinc , carbene , catalysis , chemistry , triple bond , insertion reaction , surface modification , combinatorial chemistry , photochemistry , double bond , polymer chemistry , organic chemistry , rhodium
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, ZnBr 2 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.