4.7 Article

Visible-Light-Driven Difluoromethylation of Isocyanides with S-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 16, Pages 10479-10487

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00816

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Funding

  1. Natural Science Foundation of Shenzhen [KQJSCX20180328095508144]
  2. Natural Science Foundation of Guangdong Province [2020A1515010874]

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A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic S-(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-c]pyridine, and pyrido[3,4-b]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.

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