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

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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,^a Qi Huang,^a Weidong Rao,^b Shun-Yi Wang

*^a and Shun-Jun Ji

*^a

Author affiliations

* Corresponding authors

^a 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, P. R. China
E-mail: shunyi@suda.edu.cn, shunjun@suda.edu.cn
Fax: +86-512-65880307
Tel: +86-512-65880307

^b Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

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.

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Article information

DOI: https://doi.org/10.1039/C9CC03604K
Article type: Communication
Submitted: 10 May 2019
Accepted: 11 Jun 2019
First published: 11 Jun 2019

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Chem. Commun., 2019,55, 7808-7811

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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

J. Li, Q. Huang, W. Rao, S. Wang and S. Ji, Chem. Commun., 2019, 55, 7808 DOI: 10.1039/C9CC03604K

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Chemical Communications