醋酸碘苯促进的脱氢氧化反应合成2-硫芳(烷)基苯酚及10H-吩噻嗪  

PhI(OAc)2-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines

作　　者：曹廷舒 魏向阳 罗敏 汪逸飞 潘子俊 徐程 殷国栋 Cao Tingshu;Wei Xiangyang;Luo Min;Wang Yifei;Pan Zijun;Xu Cheng;Yin Guodong(Hubei Key Laboratory of Pollutant Analysis and Reuse Technology,College of Chemistry and Chemical Engineering,Hubei Normal University,Huangshi,Hubei 435002)

机构地区：[1]湖北师范大学化学化工学院,污染物分析与资源化湖北省重点实验室,湖北黄石435002

出　　处：《有机化学》2022年第7期2079-2088,共10页Chinese Journal of Organic Chemistry

基　　金：湖北省教育厅科学技术研究(No.D20192503)资助项目。

摘　　要：报道了一种醋酸碘苯促进苯酚邻位C(sp^(2))—H与硫酚S—H之间通过氧化脱氢直接构建C—S键合成2-硫芳(烷)基苯酚衍生物的新方法.当底物为2-氨基苯硫酚时,则实现了缩合环化产物10H-吩噻嗪的高效合成.未见文献报道的新化合物均通过了^(1)H NMR、^(13)C NMR、IR和HRMS的表征,其中2-((4-溴苯基)硫代)-1,4-苯二酚(3i)的结构还通过了X-ray单晶衍射的证实.该方法原料易得、条件温和、操作简便,同时具有良好的原子经济性.A PhI(OAc)_(2)-promoted reaction for the synthesis of 2-(aryl/alkylthio)phenol derivatives has been developed,which was realized via dehydrogenation oxidation between ortho-C(sp^(2))—H of phenols and S—H of thiophenols for direct formation of C—S bonds.Particularly,this method was also successfully applied for the efficient construction of tricyclic 10H-phenothiazines using 2-aminothiophenols as the substrates.All the newly synthesized products were identified by means of ^(1)H NMR,^(13)C NMR,IR and HRMS.Besides,2-((4-bromophenyl)thio)benzene-1,4-diol(3i)was further confirmed by X-ray single crystal diffraction analysis.The method has the advantages of simple and easily available starting materials,mild reaction conditions,simple operation,as well as high atom economy.

关 键 词：2-硫芳(烷)基苯酚 10H-吩噻嗪 脱氢氧化 C—S键形成 

分 类 号：O621.3[理学—有机化学]