Iodine-Catalyzed Direct Olefination of 2‑Oxindoles and Alkenes via Cross-Dehydrogenative Coupling (CDC) in Air

A direct intermolecular olefination of sp3 C–H bond between 2-oxindoles and simple alkenes via a Cross-Dehydrogenative Coupling (CDC) strategy has been developed. In the absence of additional base, moderate to excellent yields have been obtained by using a catalytic amount of iodine with atmospheric...

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Bibliographic Details
Published in:Organic letters 2015-08, Vol.17 (15), p.3702-3705
Main Authors: Huang, Hong-Yan, Wu, Hong-Ru, Wei, Feng, Wang, Dong, Liu, Li
Format: Article
Language:English
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Summary:A direct intermolecular olefination of sp3 C–H bond between 2-oxindoles and simple alkenes via a Cross-Dehydrogenative Coupling (CDC) strategy has been developed. In the absence of additional base, moderate to excellent yields have been obtained by using a catalytic amount of iodine with atmospheric oxygen as the reoxidant. Based on the observation of a radical capture experiment, the transformation is proposed to proceed via a radical process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01662