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2024 , Vol. 44 >Issue 5: 1576 - 1583

DOI: https://doi.org/10.6023/cjoc202310026

研究论文

基于氘代二甲基亚砜(DMSO-d6)实现吲哚C(2)位选择性甲硫基化与三氘甲硫基化反应

  • 张娟 ,
  • 王奕森 ,
  • 田钰 ,
  • 徐晶 ,
  • 高文超 ,
  • 常宏宏 ,
  • 孟凡会 ,
  • 杨朋
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  • a 太原理工大学生物医学工程学院 太原 030024
    b 山西天宏达安医药科技有限公司 山西晋中 030600
    c 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
    b 山东师范大学化学化工与材料科学学院 济南 250014

收稿日期: 2023-10-26

  修回日期: 2023-12-24

  网络出版日期: 2024-01-18

基金资助

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(SKL202102); 山西省自然科学基金(20210302124123); 山西省自然科学基金(202303021211033)

收起

Regioselective C(2) Methylthiolation and d3-Methylthiolation of Indoles Based on Dimethyl Sulfoxide (DMSO-d6) Reagents

  • Juan Zhang ,
  • Yisen Wang ,
  • Yu Tian ,
  • Jing Xu ,
  • Wenchao Gao ,
  • Honghong Chang ,
  • Fanhui Meng ,
  • Peng Yang
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  • a College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024
    b Shanxi Tihondan Pharmaceutical Technology Co. Ltd., Jinzhong, Shanxi 030600
    c State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024
    b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014
*E-mail: ;
;

Received date: 2023-10-26

  Revised date: 2023-12-24

  Online published: 2024-01-18

Supported by

State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology(SKL202102); Natural Science Foundation of Shanxi Province(20210302124123); Natural Science Foundation of Shanxi Province(202303021211033)

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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-d6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.

关键词： 铜; 吲哚; 三氘甲硫基化; 甲硫基化; 二甲基亚砜(DMSO)

本文引用格式

张娟 , 王奕森 , 田钰 , 徐晶 , 高文超 , 常宏宏 , 孟凡会 , 杨朋 . 基于氘代二甲基亚砜(DMSO-d6)实现吲哚C(2)位选择性甲硫基化与三氘甲硫基化反应[J]. 有机化学, 2024 , 44(5) : 1576 -1583 . DOI: 10.6023/cjoc202310026

Abstract

Cu(OAc)2 mediated C(2)-selective d3-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 d3-methylthiolated products could also be obtained with DMSO-d6 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.

Key words： copper; indole; d3-methylthiolation; methylthiolation; dimethyl sulfoxide (DMSO)

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