Trisulfur Radical Anion (S3•-) Involved [1 + 2 + 2] and [1 + 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene and 2-Benzylidenetetrahydrothiophene Derivatives

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

doi:10.1021/acs.orglett.8b02066

Trisulfur Radical Anion (S₃^•-) Involved [1 + 2 + 2] and [1 + 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene and 2-Benzylidenetetrahydrothiophene Derivatives

Org Lett. 2018 Aug 3;20(15):4704-4708. doi: 10.1021/acs.orglett.8b02066. Epub 2018 Jul 19.

Authors

Jing-Hao Li¹, Qi Huang¹, Shun-Yi Wang¹, Shun-Jun Ji¹

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 , China.

PMID: 30024757
DOI: 10.1021/acs.orglett.8b02066

Abstract

S₃^•--mediated [1 + 2 + 2] and [1 + 3 + 1] cycloaddition reactions of aromatic alkynes to give tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives via two C-S bond formations are developed. These two protocols provide new, simple, and straightforward strategies to construct tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives under transition-metal-free conditions. This study also expands the application of S₃^•- in organic reactions.

Publication types

Research Support, Non-U.S. Gov't