α-Heteroarylation of Thioethers via Photoredox and Weak Bronsted Base Catalysis

被引：23

作者：

Alfonzo, Edwin ^{[1
]}

Hande, Sudhir M. ^{[1
]}

机构：

[1] AstraZeneca, Oncol R&D, Res & Early Dev, Med Chem, Waltham, MA 02451 USA

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 15期

关键词：

C-H FUNCTIONALIZATION; METAL-FREE; ALKYLATION; HYDROXYMETHYLATION; PYRIDINES; ETHERS; SCOPE;

D O I：

10.1021/acs.orglett.1c02151

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the C-H activation of thioethers to alpha-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of alpha-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by alpha-C-H deprotonation by a weak Bronsted base catalyst to afford alpha-thio alkyl radicals. Further, N-methoxyheteroarenium salts play additional roles as a source of methoxyl radical that contributes to alpha-thio alkyl radical generation and a sacrificial oxidant that regenerates the photoredox catalytic cycle.

引用

页码：6115 / 6120

页数：6

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