Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones via visible light-induced tandem radical cyclization of N-arylacrylamides

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Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones via visible light-induced tandem radical cyclization of N-arylacrylamides

Sun, Huan; Jiang, Yue; Yang, Ying-Sha; Li, Yun-Yun; Li, Lin; Wang, Wen-Xuan; Feng, Tao; Li, Zheng-Hui; Liu, Ji-Kai

Organic & biomolecular chemistry, 07/2019, Volume: 17, Issue: 27

Journal Article

Visible light-induced difluoromethylation of N-arylacrylamides to afford difluoromethylated 2-oxindoles and quinoline-2,4-diones with difluoromethyl 2-pyridyl sulfones as radical precursors has been disclosed. This method provides convenient access to a variety of 2-oxindoles and quinoline-2,4-diones under mild conditions via a proposed tandem radical addition/cyclization process along with good tolerance to various functional groups. In addition, preliminary experimental studies have revealed that water is a key factor in difluoromethylation and the reaction involves an oxidative quenching cycle of the photocatalyst.

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