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Iridium‐Catalyzed Regioselective Silylation of Aromatic and Benzylic CH Bonds Directed by a Secondary Amine
Author(s) -
Li Qian,
Driess Matthias,
Hartwig John F.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201404620
Subject(s) - silylation , regioselectivity , benzylamine , chemistry , iridium , aniline , amine gas treating , catalysis , organic chemistry , medicinal chemistry
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.