The Different Faces of Photoredox Catalysts: Visible-Light-Mediated Atom Transfer Radical Addition (ATRA) Reactions of Perfluoroalkyl Iodides with Styrenes and Phenylacetylenes

被引：185

作者：

Rawner, Thomas ^{[1
]}

Lutsker, Eugen ^{[1
]}

Kaiser, Christian A. ^{[1
]}

Reiser, Oliver ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany

来源：

ACS CATALYSIS | 2018年 / 8卷 / 05期

关键词：

photoredox catalysis; copper; ATRA; iodoperfluoroalkylation; visible light; ELECTRON-TRANSFER OXIDATION; TERMINAL ALKENES; FACILE SYNTHESIS; ALKYL RADICALS; TRIFLUOROMETHYLATION; COPPER; COMPLEXES; HALIDES; IODOPERFLUOROALKYLATION; MECHANISM;

D O I：

10.1021/acscatal.8b00847

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A photoredox-catalyzed procedure for the iodoper-fluoroalkylation of styrenes and phenylacetylenes using readily available copper phenanthroline catalyst is reported. In contrast to commonly employed [Ru(bpy)(3)]Cl-2, [Ru(phen)(3)]Cl-2 or fac-Ir(ppy)(3), [Cu(dap)(2)]Cl is capable to convert styrenes to the corresponding perfluoroalkyl tagged ethylbenzenes, pointing toward an additional role of the copper catalyst beyond photoinduced electron transfer. An inner sphere catalytic cycle involving Cu(III) intermediates or ligand abstraction from a [Cul](+) intermediate is proposed.

引用

页码：3950 / 3956

页数：13

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