Iridium-Catalyzed Regioselective Silylation of Aromatic and Benzylic C-H Bonds Directed by a Secondary Amine
Reported herein is an iridium-catalyzed, regioselective silylation of the aromatic CH bonds of benzylamines and the benzylic CH bonds of 2,N-dialkylanilines. In this process, (hydrido)silyl amines, generated in situ by dehydrogenative coupling of benzylamine or aniline with diethylsilane, undergo selective silylation at the CH bond γ to the amino group. The products of this silylation are suitable for subsequent oxidation, halogenation, and cross-coupling reactions to deliver benzylamine and arylamine derivatives.
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