Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds,Angewandte Chemie International Edition

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Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-11-04 , DOI: 10.1002/anie.202011400
Liubov I. Panferova ₁ , Mikhail O. Zubkov ₁ , Vladimir A. Kokorekin ₁ , Vitalij V. Levin ₁ , Alexander D. Dilman ₁

Affiliation

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.

中文翻译：

使用巯基自由基进行脂肪族氢原子转移：未活化的CH键的硫代化

描述了无金属和无催化剂的硫代自由基介导的烷烃活化作用。四氟吡啶基二硫化物用于在400 nm发光二极管照射下对CH键进行硫键化。据信，关键的CH活化步骤是通过受氟化的噻吩基影响的氢原子提取进行的。仲，叔和杂原子取代的CH键可能参与硫醇化反应。所得的硫化物在与烯烃和杂芳烃的反应中具有作为光氧化还原活性自由基前体的广泛潜力。

更新日期：2020-11-04

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