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Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner‐Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst
Author(s) -
Bagal Dattatraya B.,
Kachkovskyi Georgiy,
Knorn Matthias,
Rawner Thomas,
Bhanage Bhalchandra M.,
Reiser Oliver
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501880
Subject(s) - reagent , catalysis , copper , phenanthroline , chemistry , photochemistry , electron transfer , eosin y , dual role , visible spectrum , inner sphere electron transfer , photoredox catalysis , polymer chemistry , combinatorial chemistry , organic chemistry , photocatalysis , materials science , ion , optoelectronics
A visible‐light‐mediated procedure for the unprecedented trifluoromethylchlorosulfonylation of unactivated alkenes is presented. It uses [Cu(dap) 2 ]Cl as catalyst, and contrasts with [Ru(bpy) 3 ]Cl 2 , [Ir(ppy) 2 (dtbbpy)]PF 6 , or eosin Y that exclusively give rise to trifluoromethylchlorination of the same alkenes. It is assumed that [Cu(dap) 2 ]Cl plays a dual role, that is, acting both as an electron transfer reagent as well as coordinating the reactants in the bond forming processes.