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

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 precur...

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Veröffentlicht in:Journal of organic chemistry 2020-08, Vol.85 (16), p.10479-10487
Hauptverfasser: Qin, Wen-Bing, Xiong, Wei, Li, Xin, Chen, Jia-Yi, Lin, Li-Ting, Wong, Henry N. C, Liu, Guo-Kai
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00816