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Wiley, ChemCatChem, 7(8), p. 1373-1378, 2016

DOI: 10.1002/cctc.201501356

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Alkali-Metal-Catalyzed Cross-Dehydrogenative Couplings of Hydrosilanes with Amines

Journal article published in 2016 by Srinivas Anga, Yann Sarazin ORCID, Jean-François Carpentier, Tarun K. Panda
This paper is available in a repository.
This paper is available in a repository.

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Abstract

We report the N−H/H−Si cross-dehydrogenative coupling (CDC) of hydrosilanes and amines with high conversion (>90 %) and chemoselectivity for the production of silazanes, using group 1 metal hexamethyldisilazides [MN(SiMe3)2] (M=Li, Na, K) as precatalysts under mild conditions. [KN(SiMe3)2] showed higher activity than the congeneric lithium and sodium salts. The catalyzed CDC reaction displays a broad substrate scope. Phenylsilane and diphenylsilane react with a number of amines under ambient conditions; more elevated temperature is required for triphenylsilane to undergo CDC reactions. The intermediate lithium complex [(THF)2Li-{N(SiHPh2)(Dipp)}] (1) has been isolated and characterized in an attempt to identify the operative reaction mechanism.