A trisulfur radical anion (S3˙-) involved sulfur insertion reaction of 1,3-enynes: sulfide sources control chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides

Jing-Hao Li; Qi Huang; Weidong Rao; Shun-Yi Wang; Shun-Jun Ji

doi:10.1039/c9cc03604k

A trisulfur radical anion (S₃˙^-) involved sulfur insertion reaction of 1,3-enynes: sulfide sources control chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides

Chem Commun (Camb). 2019 Jul 2;55(54):7808-7811. doi: 10.1039/c9cc03604k.

Authors

Jing-Hao Li¹, Qi Huang, Weidong Rao, Shun-Yi Wang, Shun-Jun Ji

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, P. R. China. shunyi@suda.edu.cn shunjun@suda.edu.cn.

PMID: 31215562
DOI: 10.1039/c9cc03604k

Abstract

Cascade cyclization reactions of S3˙-in situ generated from S2- with 1,3-enynes for the chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides controlled by sulfide salts are developed. These two protocols provide new, environment-friendly and simple strategies to construct 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides via the formation of two and six C-S bonds, respectively.