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

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....

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (48), p.8771-8776
Main Authors: Dong, Xiaotong, Liu, Xiaonuo, Wang, Lei, Zhang, Yixuan, Li, Jiale, Tian, Laijin, Zhao, Yulei
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03906