Photoinduced Metal-Free Radical Addition/Cyclization of 2‑Cyanoaryl Acrylamides to Prepare gem-Difluorinated Naphthyridinone Scaffolds

Direct construction of gem-difluorinated heterocycles represents a long-standing challenge in organic chemistry. Herein, we developed a transition-metal-free photocatalytic radical addition/cyclization of BrCF2COR with 2-cyanoaryl acrylamides to give gem-difluorinated naphthyridinone scaffolds in mo...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-08, Vol.89 (15), p.10831-10843
Main Authors: Wu, Qiaoyan, Ren, Meilin, Zhou, Zhike, Xu, Yanli, Chen, Yanyan
Format: Article
Language:English
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Summary:Direct construction of gem-difluorinated heterocycles represents a long-standing challenge in organic chemistry. Herein, we developed a transition-metal-free photocatalytic radical addition/cyclization of BrCF2COR with 2-cyanoaryl acrylamides to give gem-difluorinated naphthyridinone scaffolds in moderate to good yields. Furthermore, some natural products were found to be suitable in the reaction system. The easily available substrates, mild reaction conditions, simple operation, and wide functionality tolerance show practical and environmental advantages in this method.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01112