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Journal Articles ChemCatChem Year : 2016

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

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.

Dates and versions

hal-01295515 , version 1 (31-03-2016)

Identifiers

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Srinivas Anga, Yann Sarazin, Jean-François Carpentier, Tarun K. Panda. Alkali-Metal-Catalyzed Cross-Dehydrogenative Couplings of Hydrosilanes with Amines. ChemCatChem, 2016, 8 (7), pp.1373 - 1378. ⟨10.1002/cctc.201501356⟩. ⟨hal-01295515⟩
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