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

Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds Full article

Journal

Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773

Output data

Year: 2021, Volume: 60, Number: 6, Pages: 2849-2854 Pages count : 6 DOI: 10.1002/anie.202011400

Authors

Liubov I Panferova ¹ , Mikhail O Zubkov ¹ , Vladimir A Kokorekin ¹ , Vitalij V Levin ¹ , Alexander D Dilman ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation

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.

Liubov I Panferova , Mikhail O Zubkov , Vladimir A Kokorekin , Vitalij V Levin , Alexander D Dilman
Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds
Angewandte Chemie International Edition. 2021. V.60. N6. P.2849-2854. DOI: 10.1002/anie.202011400 WOS Scopus OpenAlex

Web of science:	WOS:000598639100001
Scopus:	2-s2.0-85099771062
OpenAlex:	W3097873632

DB	Citing
OpenAlex	82
Web of science	74
Scopus	70