DOI: 10.1021/acs.joc.6c01501 ISSN: 0022-3263

Phototriggered Self-Catalyzed Multicomponent Fluoroalkylation of N -Heteroarenes with Alkenes and RfSO2Na

Ying-Li Cai, Zi-Tong Zhang, Rou Ding, Jian Li, Jun Jiang, Zi Yang, Yu-Cai Tang, Wei-Min He

Abstract

Herein, we report a sustainable protocol for the construction of diverse fluoroalkylated N-heteroarenes via a phototriggered, self-catalyzed multicomponent reaction of N-heteroarenes with alkenes and RfSO2Na, which proceeds in the absence of any exogenous photocatalyst or strong oxidant. This method features a broad substrate scope, good functional group tolerance, and operational simplicity. The application of continuous-flow technology not only significantly improves the reaction efficiency but also demonstrates promising scalability. Mechanistic studies suggest that the fluoroalkylation process involves energy transfer, sequential single-electron-transfer steps, a 1,2-hydrogen shift, and deprotonation.

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