Trifluoromethylchlorosulfonylation of alkenes: evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst.
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]Cl2, [Ir(ppy)2(dtbbpy)]PF6, 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.
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg (Germany).|Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai-400 019 (India).
Dattatraya B
DB
Bagal
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg (Germany).|Current address: Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Science of Ukraine, Murmanska str 1, 02660, Kyiv (Ukraine).
Georgiy
G
Kachkovskyi
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg (Germany).
Matthias
M
Knorn
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg (Germany).
Thomas
T
Rawner
Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai-400 019 (India).
Bhalchandra M
BM
Bhanage
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg (Germany). oliver.reiser@chemie.uni-regensburg.de.
Oliver
O
Reiser
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D008027:Light; D010084:Oxidation-Reduction; D010618:Phenanthrolines / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D056831:Coordination Complexes; D010618:Phenanthrolines; D003300:Copper; D012428:Ruthenium; C025205:1,10-phenanthroline
atom-transfer radical additions (ATRA); chlorosulfonylation; copper; photocatalysis; trifluoromethylation