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Photoredox‐Catalyzed Oxydifluoroalkylation of Styrenes for Access to Difluorinated Ketones with DMSO as an Oxidant
Author(s) -
Li Lixin,
Ma YanNa,
Tang Mi,
Guo Jing,
Yang Zhen,
Yan Yizhe,
Ma Xiantao,
Tang Lin
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900521
Subject(s) - chemistry , alkene , regioselectivity , reagent , catalysis , dimethyl sulfoxide , sulfoxide , base (topology) , photoredox catalysis , combinatorial chemistry , organic chemistry , photocatalysis , mathematical analysis , mathematics
Abstract By taking advantage of dimethyl sulfoxide (DMSO) as an oxidant, the photoredox‐catalyzed alkene oxydifluoroalkylation for formal C( sp 3 )−CF 2 R and C( sp 2 )=O formation is disclosed for the first time. This difunctionalization reaction employs readily available styrenes as the substrates and bromodifluoro compounds as the difluoroalkylating reagents, which can afford the difluorinated ketones in acceptable yields with excellent regioselectivity. Experiments indicate that fac ‐Ir(ppy) 3 ‐catalyzed oxydifluoroalkylation can proceed smoothly under base‐free conditions in the presence of AgTFA.