Copper-Catalyzed Silylation of C(sp3)-H Bonds Adjacent to Amide Nitrogen Atoms
Jian-Jun Feng1, Martin Oestreich1
1Institut für Chemie, Technische Universität Berlin , Strasse des 17. Juni 115 , 10623 Berlin , Germany.
Organic Letters
|June 30, 2018
Abstract:
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.
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