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Palladium‐Catalyzed C−H Arylation of α,β‐Unsaturated Imines: Catalyst‐Controlled Synthesis of Enamine and Allylic Amine Derivatives
Author(s) -
Li Minyan,
GonzálezEsguevillas María,
Berritt Simon,
Yang Xiaodong,
Bellomo Ana,
Walsh Patrick J.
Publication year - 2016
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.201509757
Subject(s) - enamine , catalysis , palladium , allylic rearrangement , chemistry , amine gas treating , organic chemistry , medicinal chemistry
A unique chemo‐ and regioselective α‐ and γ‐arylation of palladium azapentadienyl intermediates is presented. Two distinct catalysts and sets of conditions successfully controlled the regioselectivity of the arylation. These methods provide the first umpolung C−H functionalization of azapentadienyl palladium intermediates and enable the divergent synthesis of allylic amine and enamine derivatives, which are of significant interest in the pharmaceutical industry.