Using the Thiyl Radical for Aliphatic Hydrogen-Atom Transfer: Thiolation of Unactivated C-H Bonds

被引：80

作者：

Panferova, Liubov, I ^{[1
]}

Zubkov, Mikhail O. ^{[1
]}

Kokorekin, Vladimir A. ^{[1
]}

Levin, Vitalij V. ^{[1
]}

Dilman, Alexander ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

alkanes; C− H functionalization; photocatalysis; thiyl radicals; visible light; DECARBOXYLATIVE ALKYLATION; DIRECT ARYLATION; FUNCTIONALIZATION; ACTIVATION; AMINATION; CATALYSIS; STRATEGY; SULFIDES; ALKANES; PHOTOCATALYSIS;

D O I：

10.1002/anie.202011400

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal- and catalyst-free thiyl-radical-mediated activation of alkanes is described. Tetrafluoropyridinyl disulfide is used to perform thiolation of the C-H bonds under irradiation with 400 nm light-emitting diodes. The key C-H activation step is believed to proceed via hydrogen-atom abstraction effected by the fluorinated thiyl radical. Secondary, tertiary, and heteroatom-substituted C-H bonds can be involved in the thiolation reaction. The resulting sulfides have wide potential as photoredox-active radical precursors in reactions with alkenes and heteroarenes.

引用

页码：2849 / 2854

页数：6

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