Electrochemical oxidative CH sulfonylation of thiophenes: Site-selective access to 2-arylsulfonylthiophenes

• Published in: Tetrahedron letters Vol. 147
• Main Authors: Yang, Zhijun, Qiao, Zhi, Yu, Xianglin, Yang, Haiyue, Yuan, Mingquan, Jin, Yi
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.09.2024
• Subjects: C–H sulfonation; Electrochemical oxidative; Sulfonyl hydrazines; Thiophenes; Thiophenes; C–H sulfonation; Sulfonyl hydrazines; Electrochemical oxidative
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2024.155208

2-Arylsulfonylthiophenes represent a class of important biologically active compounds. Although methods for synthesizing C2-functionalized thiophenes have been extensively reported, research on the synthesis of 2-arylsulfonylthiophenes is extremely rare. Herein, we report a method for 2-arylsulfonylthiophenes via exogenous-oxidant-free electrochemical oxidative CH sulfonylation of thiophenes, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups. These reactions exhibit broad substrate scope (32 examples) and offer operationally simple, low-cost procedures in a single step. [Display omitted] •A novel electrochemical method enables efficient synthesis of 2-arylsulfonylthiophenes.•The electrochemical approach avoids desulfonylation and over-reduction issues.•The method offers broad substrate scope and simplicity for 2-arylsulfonylthiophenes synthesis. 2-Arylsulfonylthiophenes represent a class of important biologically active compounds. Although methods for synthesizing C2-functionalized thiophenes have been extensively reported, research on the synthesis of 2-arylsulfonylthiophenes is extremely rare. Herein, we report a method for 2-arylsulfonylthiophenes via exogenous-oxidant-free electrochemical oxidative CH sulfonylation of thiophenes, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups. These reactions exhibit broad substrate scope (32 examples) and offer operationally simple, low-cost procedures in a single step.