Visible-Light-Driven Difluoromethylation of Isocyanides with <i>S</i>-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines
Wen‐Bing Qin, Wei Xiong, Xin Li, Jiayi Chen, Liting Lin, Henry Ν. C. Wong, Guo‐Kai Liu
Abstract
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.
Topics & Concepts
ChemistryIndole testPyridineSalt (chemistry)ElectrophileCombinatorial chemistryCatalysisMedicinal chemistryOrganic chemistryFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques