Citation: Yi Yu, Yimin Jiang, Shaofen Wu, Zhaojiang Shi, Jinnan Wu, Yaofeng Yuan, Keyin Ye. Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes[J]. Chinese Chemical Letters, ;2022, 33(4): 2009-2014. doi: 10.1016/j.cclet.2021.10.016 shu

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Yi Yu ^a ,
Yimin Jiang ^a ,
Shaofen Wu ^a ,
Zhaojiang Shi ^a ,
Jinnan Wu ^a ,
Yaofeng Yuan ^{a, *} ,
Keyin Ye ^{a, b, *}

a.
Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, china
b.
State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, china

yaofeng_yuan@fzu.edu.cn

kyye@fzu.edu.cn

Received Date: 15 August 2021
Revised Date: 30 September 2021
Accepted Date: 11 October 2021
Available Online: 16 October 2021

Figures(7)

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H₂O in the reaction mixture.
- Alkene,
- Chemoselectivity,
- Electrochemistry,
- Fluorine,
- Sulfur
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