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

被引：289

作者：

Bagal, Dattatraya B. ^{[1
,2
]}

Kachkovskyi, Georgiy ^{[1
]}

Knorn, Matthias ^{[1
]}

Rawner, Thomas ^{[1
]}

Bhanage, Bhalchandra M. ^{[2
]}

Reiser, Oliver ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

[2] Inst Chem Technol Matunga, Dept Chem, Bombay 400019, Maharashtra, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 24期

关键词：

atom-transfer radical additions (ATRA); chlorosulfonylation; copper; photocatalysis; trifluoromethylation; TRANSFER RADICAL-ADDITION; VISIBLE-LIGHT; MEDICINAL CHEMISTRY; RUTHENIUM(II) COMPLEX; TRIFLUOROMETHYLATION; FLUORINE; HALIDES; BOND; SULFONAMIDES; CHLORIDES;

D O I：

10.1002/anie.201501880

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：6999 / 7002

页数：4

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