Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF3: C(sp)–SCF3 bond formation towards ynonyl trifluoromethyl sulfides

Huanfeng Jiang; Rui Zhu; Chuanle Zhu; Fulin Chen; Wanqing Wu

doi:10.1039/C8OB00007G

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Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF₃: C(sp)–SCF₃ bond formation towards ynonyl trifluoromethyl sulfides†

Huanfeng Jiang,

*^a Rui Zhu,^a Chuanle Zhu,*^ab Fulin Chen^a and Wanqing Wu^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
E-mail: cechlzhu@scut.edu.cn, jianghf@scut.edu.cn

^b State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, P. R. China

Abstract

An AgSCF₃ mediated nucleophilic trifluoromethylthiolation reaction for C(sp)–SCF₃ bond formation is reported. This nucleophilic trifluoromethylthiolation reaction of bromoalkynones afforded various useful ynonyl trifluoromethyl sulfides in high yields. Interestingly, the over-addition of AgSCF₃ is avoided in our approach.

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

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Article information

DOI: https://doi.org/10.1039/C8OB00007G
Article type: Communication
Submitted: 02 Jan 2018
Accepted: 02 Feb 2018
First published: 02 Feb 2018

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Org. Biomol. Chem., 2018,16, 1646-1650

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Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF₃: C(sp)–SCF₃ bond formation towards ynonyl trifluoromethyl sulfides

H. Jiang, R. Zhu, C. Zhu, F. Chen and W. Wu, Org. Biomol. Chem., 2018, 16, 1646 DOI: 10.1039/C8OB00007G

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Organic & Biomolecular Chemistry