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Visible-light-induced perfluoroalkylation cyclization to access perfluoroalkylated benzazepines and benzoxepines by
Anxu Pan1, Wanqing Zhao1, Cuifu Jiang1
1Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. zhounn@ahnu.edu.cn.
Abstract:
A visible-light-mediated perfluoroalkylation/cyclization of N-allyl-N-(2-(3,3-bis(methylthio)acryloyl)aryl)-4-methylbenzenesulfon-amides and 1-(2-(allyloxy)aryl)-3,3-bis(methylthio)prop-2-en-1-ones for the synthesis of perfluoroalkylated benzazepines and benzoxepines has been developed. This protocol is photocatalyst-free, and features simple operation and good regioselectivity, providing a novel environmentally friendly strategy to access the seven-membered heterocycles. Preliminary mechanistic studies reveal that the formation of EDA complexes between the perfluoroalkyl iodides and K2CO3 initiates the reaction process.
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