Co(III)-Catalyzed Annulative Vinylene Transfer via C–H Activation: Three-Step Total Synthesis of 8‑Oxopseudopalmatine and Oxopalmatine

The Co­(III)-catalyzed redox-neutral annulation of benzamides and acrylamides with vinylene carbonate for the synthesis of isoquinolinones and pyridinones has been developed. This protocol employing inexpensive Co­(III) as the catalyst tolerated diverse functional groups and substitution patterns, a...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (15), p.5925-5930
Main Authors: Li, Xinghua, Huang, Ting, Song, Ying, Qi, Yue, Li, Limin, Li, Yanping, Xiao, Qi, Zhang, Yuanfei
Format: Article
Language:English
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Summary:The Co­(III)-catalyzed redox-neutral annulation of benzamides and acrylamides with vinylene carbonate for the synthesis of isoquinolinones and pyridinones has been developed. This protocol employing inexpensive Co­(III) as the catalyst tolerated diverse functional groups and substitution patterns, affording the target products with good to excellent yields. The synthetic utility of this transformation was demonstrated by a three-step synthesis of gusanlung D, 8-oxopseudopalmatine, and oxopalmatine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02016