Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1576-1583.DOI: 10.6023/cjoc202310026 Previous Articles     Next Articles

ARTICLES

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a, 王奕森a, 田钰a, 徐晶a, 高文超a, 常宏宏a,b,*(), 孟凡会c,*(), 杨朋d,*()   

  1. 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 发布日期: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)

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

Juan Zhanga, Yisen Wanga, Yu Tiana, Jing Xua, Wenchao Gaoa, Honghong Changa,b(), Fanhui Mengc(), Peng Yangd()   

  1. 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
  • Received:2023-10-26 Revised:2023-12-24 Published:2024-01-18
  • Contact: *E-mail: changhonghong@tyut.edu.cn; mengfanhui@tyut.edu.cn; yangpeng@sdnu.edu.cn
  • 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)

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)