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Electrochemical Synthesis of β-Keto Sulfonyl Fluorides via Radical Fluorosulfonylation of Vinyl Triflates

Qingyuan Feng, Yuanyuan Fu, Yu Zheng, Saihu Liao and Shenlin Huang*

*Nanjing Forestry University, Nanjing 210037, People’s Republic of China, Email:

Q. Feng, Y. Fu, Y. Zheng, S. Liao, S. Huang, Org. Lett., 2022, 24, 3702-3706.

DOI: 10.1021/acs.orglett.2c01336

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An electroreductive protocol for the radical fluorosulfonylation of vinyl triflates with FSO2Cl as the fluorosulfonyl radical source uses inexpensive graphite felt as electrodes, thus avoiding the use of a sacrificial anode. This metal-free protocol offers mild conditions, easy scalability and provides valuable β-keto sulfonyl fluorides from readily available precursors.

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proposed mechanism

Electrochemical Synthesis of β-Ketosulfonyl Fluorides - Experimental Procedure and Reaction Setup

A three necked round bottom flask (25 mL) (Figure below) equipped with two graphite felt electrodes (20 mm x 10 mm x 1 mm), and a stir bar was charged with Et4NPF6 (421 mg, 0.15 M), anhydrous Et2O (10 mL, 0.02 M) and 1 (0.2 mmol). Then, ClSO2F was added (0.32 mmol, 1.6 eq, 1 M in anhydrous PhCF3). The mixture was electrolyzed at a constant voltage of 15 V for 6 h. Subsequently, the reaction was quenched with water and electrodes were rinsed with EtOAc. The resulting mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography to afford the desired product.

(A) and (B) Graphite felt electrode (20 mm x 10 mm x 1 mm). (C) and (D) Standard reaction unit. (E) The reaction mixture after 6 h of electrolysis.

Key Words

sulfonyl fluorides, electrochemistry

ID: J54-Y2022