有机化学ChineseJournalofOrganicChemistryARTICLE*Correspondingauthors.E-mail:aarexit@xjnu.edu.cn;zengjing800111@163.comReceivedMay7,2022;revisedAugust1,2022;publishedonlineAugust25,2022.ProjectsupportedbytheScientificResearchProgramoftheHigherEducationInstitutionofXinjiang(No.XJEDU2020I015).新疆维吾尔自治区高校科研计划自然科学重点(No.XJEDU2020I015)资助项目.236http://sioc-journal.cn/©2023ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciencesChin.J.Org.Chem.2023,43,236～243DOI:10.6023/cjoc202205010研究论文硫代磺酸酯和磺酰卤的绿色合成研究乃比江•赛米张蕾买地娜•沙拉木曾竟*阿布都热西提•阿布力克木*(新疆师范大学化学系乌鲁木齐830054)摘要利用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1HNMR、13CNMR结构确证.关键词一锅法;2-碘酰基苯甲酸(IBX);卤化;绿色合成GreenSynthesisofThiosulfonatesandSulfonylHalidesNaibijiang,SaimiZhang,LeiMaidina,ShalamuZeng,Jing*Abulikemu,AbuduRexit*(DepartmentofChemistry,XinjiangNormalUniversity,Urumqi830054)AbstractUsingtheoxidationbetween2-iodoylbenzoicacid(IBX)andtetrabutylammoniumbromide(TBAB),thiophenolsandthiolsreactedrapidlytoformcorrespondingthiosulfonatesatroomtemperature,and11thiosulfonateswereobtainedwithyieldsrangingfrom54%to83%.ItwasalsofoundthatthecatalyticsysteminthepresenceofaqueousHCl(w＝36%)andHBr(w＝46%)oxidativelyhalogenatedthiophenolsandthiols,respectively,11kindsofsulfonylchloridesand11kindsofsulfonylbromideswereobtainedwithyieldsrangingfrom62%to84%.Themethodhastheadvantagesofsimpleandeffi-cient,simplepost-treatment,greenoxidantandsolvent,mildconditions,etc.Allproductswereconfirmedby1HNMR,13CNMRstructure.Keywordsone-potreaction;2-iodoylbenzoicacid(IBX);h...
