Pd-Catalyzed Spirocyclization via C–H Activation and Benzyne Insertion

A palladium-catalyzed spirocyclization forming spirooxindoles and spirodihydrobenzofurans has been achieved. Mechanistic studies suggest that the transformation proceeds through sequential carbopalladation, C–H activation, and benzyne insertion. Both classes of spirocycles have been synthesized in g...

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Bibliographic Details
Published in:Organic letters 2016-12, Vol.18 (24), p.6324-6327
Main Authors: Yoon, Hyung, Lossouarn, Alexis, Landau, Felicitas, Lautens, Mark
Format: Article
Language:English
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Summary:A palladium-catalyzed spirocyclization forming spirooxindoles and spirodihydrobenzofurans has been achieved. Mechanistic studies suggest that the transformation proceeds through sequential carbopalladation, C–H activation, and benzyne insertion. Both classes of spirocycles have been synthesized in good to excellent yields, and the procedure is readily scalable.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03213