Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst

Bagal, Dattatraya B. and Kachkovskyi, Georgiy and Knorn, Matthias and Rawner, Thomas and Bhanage, Bhalchandra M. and Reiser, Oliver (2015) Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 54 (24). pp. 6999-7002. ISSN 1433-7851, 1521-3773

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Abstract

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)]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.

Item Type: Article
Uncontrolled Keywords: TRANSFER RADICAL-ADDITION; VISIBLE-LIGHT; MEDICINAL CHEMISTRY; RUTHENIUM(II) COMPLEX; TRIFLUOROMETHYLATION; FLUORINE; HALIDES; BOND; SULFONAMIDES; CHLORIDES; atom-transfer radical additions (ATRA); chlorosulfonylation; copper; photocatalysis; trifluoromethylation
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 11 Jul 2019 09:48
Last Modified: 11 Jul 2019 09:48
URI: https://pred.uni-regensburg.de/id/eprint/5325

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