Metal-Free Cyanation of gem-Difluoroalkenes via Azide-Mediated C–C Double Bond Fragmentation

Activation and cleavage of C–C double bonds are long-standing challenges in synthetic chemistry. Herein, we report an unprecedented azide-mediated C–C double bond fragmentation of gem-difluoroalkenes under mild and metal-free conditions, enabling the efficient synthesis of structurally diverse aroma...

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Published inJournal of organic chemistry Vol. 89; no. 11; pp. 7609 - 7617
Main Authors Wang, Hui, He, Yuan-Yuan, Han, Jianwei, Zhou, Zhong-Qiang, Hu, Xiao-Qiang
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 24.05.2024
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Summary:Activation and cleavage of C–C double bonds are long-standing challenges in synthetic chemistry. Herein, we report an unprecedented azide-mediated C–C double bond fragmentation of gem-difluoroalkenes under mild and metal-free conditions, enabling the efficient synthesis of structurally diverse aromatic nitriles in moderate to good yields. This protocol is also amenable to the cyanation of gem-dichloro and dibromo alkenes. This reaction features simple operation and good functional group compatibility and can be implemented at a gram scale.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00281