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Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds
Author(s) -
Panferova Liubov I.,
Zubkov Mikhail O.,
Kokorekin Vladimir A.,
Levin Vitalij V.,
Dilman Alexander D.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011400
Subject(s) - chemistry , photochemistry , hydrogen atom abstraction , catalysis , disulfide bond , heteroatom , hydrogen atom , hydrogen bond , hydrogen , molecule , organic chemistry , alkyl , biochemistry
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.