Transition-metal-free direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2

被引：33
|
作者：
Zhao, Xia [1 ]
Zheng, Xiancai [1 ]
Tian, Miaomiao [1 ]
Sheng, Jianqiao [1 ]
Tong, Yifan [1 ]
Lu, Kui [2 ]
机构：
[1] Tianjin Normal Univ, Minist Educ, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Tianjin Key Lab Struct & Performance Funct Mol,Co, Tianjin 300387, Peoples R China
[2] Tianjin Univ Sci & Technol, Coll Biotechnol, Tianjin 300457, Peoples R China
来源：
TETRAHEDRON | 2017年 / 73卷 / 51期
基金：
美国国家科学基金会;
关键词：
Trifluoromethylthiolation; CF3SO2Na; PhPCl2; Indole; Electron-rich aromatics; HYPERVALENT IODINE REAGENT; SODIUM TRIFLUOROMETHANESULFINATE; SULFONYL HYDRAZIDES; THIOLATION; CHLORIDE; DIFLUOROMETHYLTHIOLATION; PYRAZOLONES; THIOETHERS; INDOLES; ACIDS;
D O I：
10.1016/j.tet.2017.11.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel transition metal-free route for the direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2 was developed. More specifically, PhPCl2 was used as both a reducing and a chlorinating reagent for the first time in this CF3SO2Na-based trifluoromethylthiolation reaction. The absence of transition metals and the use of cheap and readily available reagents render this method an alternative and practical strategy for the trifluoromethylthiolation of electron-rich aromatics. (C) 2017 Published by Elsevier Ltd.
引用
收藏
页码：7233 / 7238
页数：6
相关论文
共 50 条
  • [1] Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF3SO2Na in the Presence of PCl3
    Zhao, Xia
    Wei, Aoqi
    Yang, Bo
    Li, Tianjiao
    Li, Quan
    Qiu, Di
    Lu, Kui
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17): : 9175 - 9181
  • [2] Copper-Promoted Trifluoromethylthiolation of Anilines with CF3SO2Na
    Mumtaz, Yasir
    Liu, Jie
    Huang, Xin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (02) : 679 - 685
  • [3] Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp2)-H Bonds with CF3SO2Na and RfSO2Na
    Jiang, Lvqi
    Qian, Jinlong
    Yi, Wenbin
    Lu, Guoping
    Cai, Chun
    Zhang, Wei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14965 - 14969
  • [4] Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride
    Zhao, Xia
    Wei, Aoqi
    Li, Tianjiao
    Su, Zhiyang
    Chen, Jun
    Lu, Kui
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 232 - 235
  • [5] Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position
    Xie, Jiao-Jiao
    Wang, Zhi-Qing
    Jiang, Guo-Fang
    RSC ADVANCES, 2019, 9 (60) : 35098 - 35101
  • [6] POCl3-Promoted Trifluoromethylthiolation-Based Vicinal Bifunctionalization of Indoles with CF3SO2Na
    Sun, Dong-Wei
    Jiang, Xu
    Jiang, Min
    Lin, Yun
    Liu, Jin-Tao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (18) : 2078 - 2081
  • [7] Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides
    Yang, Yi
    Xu, Long
    Yu, Siqi
    Liu, Xiaoqiang
    Zhang, Yu
    Vicic, David A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (03) : 858 - 863
  • [8] External-Oxidant-Free Electrochemical Oxidative Trifluoromethylation of Arenes Using CF3SO2Na as the CF3 Source
    Deng, Yong
    Lu, Fangling
    You, Siqi
    Xia, Tianrui
    Zheng, Yifan
    Lu, Cuifen
    Yang, Guichun
    Chen, Zuxing
    Gao, Meng
    Lei, Aiwen
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (08) : 817 - 820
  • [9] Free-radical promoted bromotrifluoromethylation of arylalkynes with CF3SO2Na and NaBrO3
    Shang, Xiao-Jie
    Luo, Rui
    Zhu, Jing
    Liu, Zhong-Quan
    TETRAHEDRON LETTERS, 2021, 62
  • [10] Electrochemically mediated trifluoromethylation of 2H-indazole derivatives using CF3SO2Na
    Wei, Tingting
    Wang, Kai
    Yu, Zhichen
    Hou, Jiahao
    Xie, Yuanyuan
    TETRAHEDRON LETTERS, 2021, 86
12345