Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 27, Pages 7930-7934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703319
Keywords
carbenes; cyclopropenes; Si-H bond functionalization; silanes; zinc catalysis
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Funding
- Ministerio de Economia y Competitividad (MINECO)
- Agencia Estatal de Investigacion (AEI)
- Fondo Europeo de Desarrollo Regional (FEDER) [CTQ2013-41511-P, CTQ2016-76840-R]
- Principado de Asturias [GRUPIN14-013]
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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.
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