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

Authors :
Qin, Wen-Bing
Xiong, Wei
Li, Xin
Chen, Jia-Yi
Lin, Li-Ting
Wong, Henry N. C.
Liu, Guo-Kai
Source :
The Journal of Organic Chemistry; August 2020, Vol. 85 Issue: 16 p10479-10487, 9p
Publication Year :
2020

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.

Details

Language :
English
ISSN :
00223263
Volume :
85
Issue :
16
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs53783775
Full Text :
https://doi.org/10.1021/acs.joc.0c00816