Electrochemical Benzylic C─H Sulfation beyond the <i>O</i> ‐Sulfonation Limitation

W Wei Sheng H Huanhuan Peng (State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China) B Ben Gao (State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China) C Chunlan Song (State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering) J Jiakun Li (State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering)

Abstract

Abstract Direct C─H sulfation represents a valuable transformation for the synthesis of organosulfates. However, it has been challenging to achieve owing to the presence of multiple C─H bonds with comparable strengths and steric environments. Current methods for producing organosulfates primarily rely on O ‐sulfonation, which limits their applicability to hydroxyl‐containing compounds. Herein, we report a practical and cost‐efficient method for the electrochemical sulfation of benzylic C─H bonds. This reaction avoids the need for strong oxidants, demonstrating broad substrate scope, excellent chemoselectivity, and site selectivity. The orthogonal reactivity of this protocol is particularly evident in the transformation of alcohol substrates.

Article Details

Volume / Issue Vol. 64, Issue 29
Published July 14, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (5)

W

Wei Sheng

H

Huanhuan Peng

State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China

B

Ben Gao

State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

C

Chunlan Song

State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering

J

Jiakun Li

State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering