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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.
Qin, Wen-Bing; Xiong, Wei; Li, Xin; Chen, Jia-Yi; Lin, Li-Ting; Wong, Henry N C; Liu, Guo-Kai.
Affiliation
  • Qin WB; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
  • Xiong W; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
  • Li X; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
  • Chen JY; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
  • Lin LT; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
  • Wong HNC; Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
  • Liu GK; School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.
J Org Chem ; 85(16): 10479-10487, 2020 Aug 21.
Article in En | MEDLINE | ID: mdl-32668153
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.

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2020 Document type: Article Affiliation country: China Country of publication: United States

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2020 Document type: Article Affiliation country: China Country of publication: United States