硫代磺酸酯和磺酰卤的绿色合成研究
收稿日期: 2022-05-07
修回日期: 2022-08-01
网络出版日期: 2022-08-25
基金资助
新疆维吾尔自治区高校科研计划自然科学重点(XJEDU2020I015)
Green Synthesis of Thiosulfonates and Sulfonyl Halides
Received date: 2022-05-07
Revised date: 2022-08-01
Online published: 2022-08-25
Supported by
Scientific Research Program of the Higher Education Institution of Xinjiang(XJEDU2020I015)
利用2-碘酰基苯甲酸(IBX)的氧化作用, 在四丁基溴化铵(TBAB)作为添加剂的条件下, 硫酚、硫醇类化合物在室温快速反应生成相应的硫代磺酸酯类化合物, 共获得了11个硫代磺酸酯, 产率为54%~83%; 而该氧化体系在加入浓盐酸(w=36%)或浓氢溴酸(w=46%)的条件下, 硫酚或硫醇均顺利被氧化卤代成相应的磺酰氯或磺酰溴, 分别获得了11个磺酰氯和11个磺酰溴产物, 产率为62%~84%. 这两种体系都简单、高效, 使用了绿色氧化剂和溶剂、具有处理简单、条件温和等优点, 所有合成产物均经1H NMR、13C NMR结构确证.
关键词： 一锅法; 2-碘酰基苯甲酸(IBX); 卤化; 绿色合成
乃比江•赛米 , 张蕾 , 买地娜•沙拉木 , 曾竟 , 阿布都热西提•阿布力克木 . 硫代磺酸酯和磺酰卤的绿色合成研究[J]. 有机化学, 2023 , 43(1) : 236 -243 . DOI: 10.6023/cjoc202205010
Using the oxidation between 2-iodoylbenzoic acid (IBX) and tetrabutylammonium bromide (TBAB), thiophenols and thiols reacted rapidly to form corresponding thiosulfonates at room temperature, and 11 thiosulfonates were obtained with yields ranging from 54% to 83%. It was also found that the catalytic system in the presence of aqueous HCl (w=36%) and HBr (w=46%) oxidatively halogenated thiophenols and thiols, respectively, 11 kinds of sulfonyl chlorides and 11 kinds of sulfonyl bromides were obtained with yields ranging from 62% to 84%. The method has the advantages of simple and efficient, simple post-treatment, green oxidant and solvent, mild conditions, etc. All products were confirmed by 1H NMR, 13C NMR structure.
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