基于氘代二甲基亚砜(DMSO-d_(6))实现吲哚C(2)位选择性甲硫基化与三氘甲硫基化反应  

Regioselective C(2)Methylthiolation and d_(3)-Methylthiolation of Indoles Based on Dimethyl Sulfoxide(DMSO-d_(6))Reagents

作　　者：张娟 王奕森 田钰 徐晶 高文超 常宏宏 孟凡会[3] 杨朋 Zhang Juan;Wang Yisen;Tian Yu;Xu Jing;Gao Wenchao;Chang Honghong;Meng Fanhui;Yang Peng(College of Biomedical Engineering,Taiyuan University of Technology,Taiyuan 030024;Shanxi Tihondan Pharmaceutical Technology Co.Ltd.,Jinzhong,Shanxi 030600;State Key Laboratory of Clean and Efficient Coal Utilization,Taiyuan University of Technology,Taiyuan 030024;College of Chemistry,Chemical Engineering and Materials Science,Shandong Normal University,Jinan 250014)

机构地区：[1]太原理工大学生物医学工程学院,太原030024 [2]山西天宏达安医药科技有限公司,山西晋中030600 [3]太原理工大学省部共建煤基能源清洁高效利用国家重点实验室,太原030024 [4]山东师范大学化学化工与材料科学学院,济南250014

出　　处：《有机化学》2024年第5期1576-1583,共8页Chinese Journal of Organic Chemistry

基　　金：太原理工大学省部共建煤基能源清洁高效利用国家重点实验室开放基金(No.SKL202102);山西省自然科学基金(Nos.20210302124123,202303021211033)资助项目。

摘　　要：发展了一种Cu(OAc)_(2)介导吲哚衍生物的C(2)选择性甲硫基化与三氘甲硫基化反应.该转化以二甲基亚砜(DMSO)作为甲硫基来源与溶剂,以中等至良好收率得到C(2)-甲硫基取代吲哚,当选用DMSO-d_(6)作为反应试剂时,也可合成得到C(2)-三氘甲硫基取代吲哚.同时,该反应不依赖于高温条件,转化可能涉及自由基途径.Cu(OAc)_(2)mediated C(2)-selective d_(3)-methylthiolation and methylthiolation of indoles were developed.With the choice of dimethyl sulfoxide(DMSO)as sulfur source and solvent,methylthiolation reaction could be achieved in moderate to good yields,and d_(3)-methylthiolated products could also be obtained with DMSO-d_(6)as reagent just by prolong the reaction time.Moreover,this methylthiolation didn't depend on high temperature,and radical pathway might be involved in this transformation.

关 键 词：铜 吲哚 三氘甲硫基化 甲硫基化 二甲基亚砜(DMSO) 

分 类 号：O626[理学—有机化学]