Oxidant- and Catalyst-Free Synthesis of Sulfonated Benzothiophenes via Electrooxidative Tandem Cyclization

Dong Zhang, Jinlin Cai, Jinze Du, Xujia Wang, Wei He, Zhao Yang, Chengkou Liu*, Zheng Fang* and Kai Guo

*College of Biotechnology and Pharmaceutical Engineering Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, China, Email: liuchengkounjtech.edu.cn, fzcpunjtech.edu.cn

D. Zhang, J. Cai, J. Du, X. Wang, W. He, Z. Yang, C. Liu, Z. Fang, K. Guo, J. Org. Chem., 2021, 86, 2593-2601.

DOI: 10.1021/acs.joc.0c02679

---

see article for more reactions

Abstract

A practical and efficient electrochemical method enables a green synthesis of C-3-sulfonated benzothiophenes in good yields from 2-alkynylthioanisoles and sodium sulfinates under oxidant- and catalyst-free conditions. Preliminary mechanistic studies indicated a tandem radical addition-cyclization pathway. Moreover, the protocol is easy to scale up.

see article for more examples

proposed mechanism

---

---

Key Words

benzothiophenes, electrochemistry

---

ID: J42-Y2021