Iridium-Catalyzed Regioselective Silylation of Aromatic and Benzylic C-H Bonds Directed by a Secondary Amine

Iridium-Catalyzed Regioselective Silylation of Aromatic and Benzylic C-H Bonds Directed by a Secondary Amine

Angew. Chem. Int. Ed.  201453,  1-5.

Reported herein is an iridium-catalyzed, regioselective silylation of the aromatic C[BOND]H bonds of benzylamines and the benzylic C[BOND]H 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 C[BOND]H 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. Read more on publisher's site.