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
  • [21] Synthesis of CF3CH2-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes
    Liang, Deqiang
    Dong, Qishan
    Xu, Penghui
    Doug, Ying
    Li, Weili
    Ma, Yinhai
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 11978 - 11986
  • [22] In Situ Generation of PhI+CF3 and Transition-Metal-Free Oxidative sp2 CH Trifluoromethylation
    Xu, Cong
    Liu, Jingxin
    Ming, Wenbo
    Liu, Yingjie
    Liu, Jun
    Wang, Mang
    Liu, Qun
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (28) : 9104 - 9109
  • [23] Synthesis of C-3-Functionalized Imidazo[1,2-a]pyridines via Direct para-Position Arylation of Electron-Rich Anilines under Transition-Metal-Free Conditions
    Hao, Liqiang
    Wu, Gaorong
    Wang, Yangyang
    Xu, Xiaobo
    Ji, Yafei
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (13) : 2159 - 2164
  • [24] Photocatalytic transition-metal-free direct 3-alkylation of 2-aryl-2H-indazoles in dimethyl carbonate
    Ma, Chunhua
    Feng, Zhiwen
    Li, Jing
    Zhang, Dandan
    Li, Wei
    Jiang, Yuqin
    Yu, Bing
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13): : 3286 - 3291
  • [25] Metal-free, Visible-Light-Induced Radical Trifluoromethylation/Cyclization of N-benzamides with CF3SO2Na to Synthesize CF3-Containing Isoquinoline-1,3-diones
    Wang, Shaowei
    Dai, Peng
    Yan, Zhichao
    Wang, Youjia
    Shao, Jiaxuan
    Wu, Yanhui
    Deng, Chao
    Zhang, Weihua
    CHEMISTRYSELECT, 2019, 4 (35): : 10329 - 10333
  • [26] Transition-metal-free Baeyer-Villiger oxidation of benzaldehydes to phenols using Na2S2O8
    Li, Wei
    Chen, Lin-Lin
    Han, Ke
    Liu, Zhi-Bin
    Luan, You-Shun
    Chen, Deng-Tai
    JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (3-4) : 115 - 118
  • [27] Direct Transition-Metal-Free Enantioselective Hydroxylation: Expeditious Access to 3-Functionalized 3-Hydroxy-2-oxindoles
    Zhao, Shouqin
    Yang, Wen
    Lan, Yunfei
    Zhao, Yanteng
    Xu, Yi
    Liu, Wanqing
    Wang, Linlin
    Zhou, Xin
    Yu, Changyan
    Guo, Ting
    Yuan, Lujiang
    Jia, Qianfa
    Ren, Qiao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (11)
  • [28] Gas-Phase Acidities of α- and α,α-SO2CF3-Substituted Toluenes. Varying Resonance Demand in the Electron-Rich System
    Zhang, Min
    Badal, Md. Mizanur Rahman
    Koppel, Ilmar A.
    Mishima, Masaaki
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2013, 86 (07) : 813 - 820
  • [29] Photocatalytic Transition-Metal-Free Direct 3-Acetalation of Quinoxaline-2(1H)-ones
    Ma, Chunhua
    Meng, Hui
    Li, Jing
    Yang, Xianguang
    Jiang, Yuqin
    Yu, Bing
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (22) : 2655 - 2662
  • [30] Efficient and Direct Selenocyanation of Ketene Dithioacetals Using Malononitrile-SeO2 Under Transition-Metal-Free Conditions
    Rai, Vishakha
    Sorabad, Ganesh S.
    Maddani, Mahagundappa R.
    CHEMISTRYSELECT, 2021, 6 (25): : 6468 - 6471
12345