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

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-dione...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-07, Vol.17 (27), p.6629-6638
Main Authors: Sun, Huan, Jiang, Yue, Yang, Ying-Sha, Li, Yun-Yun, Li, Lin, Wang, Wen-Xuan, Feng, Tao, Li, Zheng-Hui, Liu, Ji-Kai
Format: Article
Language:English
Subjects:
Functional groups
Light effects
Quinoline
Sulfones
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01213c