Palladium-Catalyzed Dearomative Cyclocarbonylation by C-N Bond Activation.

Abstract

A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2 ], 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 CN bond activation, dearomatization, CO insertion, and a Heck reaction.

• Authors: Hui Yu, Guoying Zhang, Hanmin Huang
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 54 Issue 37 Pg. 10912-6 (Sep 07 2015) ISSN: 1521-3773 [Electronic] Germany
• PMID: 26200664 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Ketones
• Palladium

Topics

• Catalysis
• Cyclization
• Ketones (chemistry)
• Palladium (chemistry)