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Visible‐Light Photoredox‐Catalyzed and Copper‐Promoted Trifluoromethoxylation of Arenediazonium Tetrafluoroborates
Author(s) -
Yang Shaoqiang,
Chen Miao,
Tang Pingping
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901447
Subject(s) - photoredox catalysis , reagent , chemistry , copper , catalysis , visible spectrum , aryl , photochemistry , trifluoromethyl , combinatorial chemistry , trifluoromethylation , reaction conditions , organic chemistry , photocatalysis , materials science , alkyl , optoelectronics
Abstract We report the development of photoredox‐catalyzed and copper‐promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible‐light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper‐promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF 3 ) 2 ] intermediate might be generated during the reaction.