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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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01295515
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Submitted on : Thursday, March 31, 2016 - 11:13:42 AM
Last modification on : Friday, July 10, 2020 - 4:25:39 PM

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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, Wiley, 2016, 8 (7), pp.1373 - 1378. ⟨10.1002/cctc.201501356⟩. ⟨hal-01295515⟩

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