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. 2014 Aug 4;53(32):8471-4.
doi: 10.1002/anie.201404620. Epub 2014 Jun 24.

Iridium-catalyzed regioselective silylation of aromatic and benzylic C-H bonds directed by a secondary amine

Qian Li  1 , Matthias Driess, John F Hartwig
Affiliations

Iridium-catalyzed regioselective silylation of aromatic and benzylic C-H bonds directed by a secondary amine

Qian Li et al. Angew Chem Int Ed Engl. .

Abstract

Reported herein is an iridium-catalyzed, regioselective silylation of the aromatic C-H bonds of benzylamines and the benzylic C-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-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.

Keywords: CH activation; arenes; iridium; oxidation; silane.

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