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Copper-Catalyzed Silylation of C(sp3)–H Bonds Adjacent to Amide Nitrogen Atoms

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journal contribution
posted on 28.06.2018, 20:16 by Jian-Jun Feng, Martin Oestreich
A copper-catalyzed C–Si bond formation between N-halogenated amides and Si–B reagents is described. This oxidative coupling enables the silylation of C­(sp3)–H bonds α to an amide nitrogen atom. The utility of the new method is demonstrated for sulfonamides, and N-chlorination with tBuOCl and C–H silylation employing CuSCN/4,4′-dimethoxy-2,2′-bipyridine as catalyst can be performed without purification of the N–Cl intermediate.