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从N-取代硫代氨基甲酸盐出发合成不对称硫代磺酸酯:轻松构建S-SO键

Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted -Thiocarbamates: Easy Access to the S-SO Bond.

作者信息

Yang Cheng-Li, Gao Xue-Jie, Jiang Xin-Yi, Shi Zhen, Hao Er-Jun, Dong Zhi-Bing

机构信息

School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, China.

Hubei Key Laboratory of Biologic Resources Protection and Utilization, Hubei Minzu University, Enshi 445000, China.

出版信息

J Org Chem. 2022 Sep 2;87(17):11656-11668. doi: 10.1021/acs.joc.2c01301. Epub 2022 Aug 12.

DOI:10.1021/acs.joc.2c01301
PMID:35959946
Abstract

Using phenyliodine diacetate as an oxidant and nickel acetate as a promoter, a wide range of unsymmetric thiosulfonates could be furnished easily in moderate to excellent yields starting from N-substituted -thiocarbamates and sodium sulfinates. This protocol features mild conditions, short reaction times, and high atomic utilization, which can provide an alternative method for the synthesis of unsymmetric thiosulfonates. In addition, the reaction could be scaled up on a gram scale, showing potential application value in industry.

摘要

以二乙酸碘苯为氧化剂、乙酸镍为促进剂,从N-取代硫代氨基甲酸盐和亚磺酸钠出发,能够轻松地以中等至优异的产率制备出多种不对称硫代磺酸酯。该方法具有条件温和、反应时间短和原子利用率高的特点,可为不对称硫代磺酸酯的合成提供一种替代方法。此外,该反应可放大至克级规模,在工业上显示出潜在的应用价值。

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