Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H2O2 promoted tandem oxidative annulation and 1,2-sulfur migration

Teng Han; Xiaoyan Luo

doi:10.1039/C8OB01835A

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Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H₂O₂ promoted tandem oxidative annulation and 1,2-sulfur migration†

Teng Han^a and Xiaoyan Luo

*^a

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* Corresponding authors

^a School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China
E-mail: xyluo@ecust.edu.cn

Abstract

A novel TBAI-catalyzed tandem thio-Michael addition/oxidative annulation of allenes and thioamides for the construction of polysubstituted 2-arylthiophenes under a sulfur migration transformation protocol has been developed. The transition-metal-free protocol achieves the oxidative cyclization reaction of thioamides containing electron-rich substituents with allenes to construct polysubstituted thiophenes selectively by controlling oxidation conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB01835A
Article type: Communication
Submitted: 30 Jul 2018
Accepted: 02 Sep 2018
First published: 03 Sep 2018

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Org. Biomol. Chem., 2018,16, 8253-8257

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Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H₂O₂ promoted tandem oxidative annulation and 1,2-sulfur migration

T. Han and X. Luo, Org. Biomol. Chem., 2018, 16, 8253 DOI: 10.1039/C8OB01835A

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Organic & Biomolecular Chemistry