Citation: Xinhua Wang, Wei Zhou, Wenlin Xie, Qi Chen, Jie Wu. Generation of (E)-β-trifluoromethyl vinylsulfonohydrazides under photocatalysis and their anti-bacteria activity[J]. Chinese Chemical Letters, ;2023, 34(6): 107984. doi: 10.1016/j.cclet.2022.107984 shu

Generation of (E)-β-trifluoromethyl vinylsulfonohydrazides under photocatalysis and their anti-bacteria activity

Xinhua Wang ^{a, 1} ,
Wei Zhou ^{b, 1} ,
Wenlin Xie ^e ,
Qi Chen ^{a, *,} ,
Jie Wu ^{a, c, d, *,}

a.
Taizhou Central Hospital (Taizhou University Hospital) & School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
b.
Department of Chemistry, Fudan University, Shanghai 200438, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
e.
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China

chenq@tzc.edu.cn

jie_wu@fudan.edu.cn

Received Date: 23 September 2022
Revised Date: 26 October 2022
Accepted Date: 3 November 2022
Available Online: 5 November 2022

Figures(2)

Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfonohydrazides in moderate to good yields. This multicomponent reaction of trifluoromethyl thianthrenium triflate, alkynes, sulfur dioxide and hydrazines proceeds efficiently under visible light irradiation in the presence of photocatalyst at room temperature with broad substrate scope and excellent functional group compatibility. This reaction is highly stereoselective, and only (E)-isomers are obtained. Additionally, these trifluoromethyl-substituted vinyl sulfonohydrazides are further evaluated for anti-bacteria activity. In vitro activities of these compounds against Staphylococcus aureus (G⁺) and Escherichia coli (G⁻) are examined.
- Alkyne,
- Hydrazine,
- Photocatalysis,
- Sulfur dioxide,
- Trifluoromethyl thianthrenium triflate
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