Palladium-Catalyzed Regioselective Carbonylation of C–H Bonds of N‑Alkyl Anilines for Synthesis of Isatoic Anhydrides

A Pd-catalyzed regioselective C–H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-10, Vol.134 (42), p.17490-17493
Main Authors: Guan, Zheng-Hui, Chen, Ming, Ren, Zhi-Hui
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Catalysis
Molecular Structure
Organometallic Compounds - chemistry
Oxazines - chemical synthesis
Oxazines - chemistry
Palladium - chemistry
Stereoisomerism
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Summary:A Pd-catalyzed regioselective C–H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja308976x