Catalyst-free gem-chlorosulfurization of difluoromethyl-substituted diazo compounds with disulfide and PhICl2

Jiuling Li; Bin Li; Juan Chen; Xinyu Jia; Min Wang; Chengjun Hao; Xinhua Zheng; Hongmei Dai; Wenhao Hu

doi:10.1039/D1OB01422F

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Catalyst-free gem-chlorosulfurization of difluoromethyl-substituted diazo compounds with disulfide and PhICl₂†

Jiuling Li,

^ab Bin Li,^b Juan Chen,^b Xinyu Jia,^b Min Wang,^b Chengjun Hao,^b Xinhua Zheng,*^b Hongmei Dai^b and Wenhao Hu*^a

Author affiliations

* Corresponding authors

^a Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
E-mail: huwh9@mail.sysu.edu.cn

^b Henan Engineering Research Center of Funiu Mountain's Medical Resources Utilization and Molecular Medicine, School of Medical Sciences, Pingdingshan University, Pingdingshan 467000, China
E-mail: zhengxinhua70@163.com

Abstract

A series of gem-chlorosulfurization products bearing difluoromethyl substituents were synthesized in high to excellent yields directly from p-toluenesulfonyl difluorodiazoethane (TsCF₂CHN₂), disulfides and PhICl₂ without any catalysts or additives. The mild reaction conditions and high functional group compatibility indicated the utility and sustainability of the method. In addition, the gem-chlorosulfurization products could be efficiently converted to sulfur-containing and aryl substituted difluoromethyl derivatives by a feasible multi-component operation.

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Article information

DOI: https://doi.org/10.1039/D1OB01422F
Article type: Communication
Submitted: 21 Jul 2021
Accepted: 26 Aug 2021
First published: 26 Aug 2021

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Org. Biomol. Chem., 2021,19, 8030-8034

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Catalyst-free gem-chlorosulfurization of difluoromethyl-substituted diazo compounds with disulfide and PhICl₂

J. Li, B. Li, J. Chen, X. Jia, M. Wang, C. Hao, X. Zheng, H. Dai and W. Hu, Org. Biomol. Chem., 2021, 19, 8030 DOI: 10.1039/D1OB01422F

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Organic & Biomolecular Chemistry