Abstract 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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