Catalyst-Free -Difluorination/Spirocyclization of Indole-2-carboxamides: Synthesis of C2-Spiroindoline Derivatives.

Org Lett

Key Laboratory of Life-Organic Analysis of Shandong Province, Key Laboratory of Green Natural Products and Pharmaceutical Intermediates in Universities of Shandong Province, Key Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu City, Shandong Province 273165, P. R. China.

Published: December 2023

A catalyst-free -difluorination/spirocyclization reaction has been successfully developed for the synthesis of -difluorinated C2-spiroindoline derivatives from indole-2-carboxamides. The resulting -difluorinated C2-spiroindolines can be easily converted into 2-spiropseudoindoxyls through hydrolysis. This method offers the benefits of simple operation, convenient access to raw materials, and mild conditions. Dual function of Selectfluor in this reaction is noteworthy as it can serve as both a fluorinating agent and an alkaline accelerator precursor.

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http://dx.doi.org/10.1021/acs.orglett.3c03906DOI Listing

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