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Palladium‐Catalyzed Dearomative Cyclocarbonylation by CN Bond Activation
Author(s) -
Yu Hui,
Zhang Guoying,
Huang Hanmin
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504805
Subject(s) - palladium , carbonylation , xantphos , intramolecular force , catalysis , chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , carbon monoxide
A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I 2 ], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene‐substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction.