Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF3SO2Na in the Presence of PCl3

被引：58

作者：

Zhao, Xia ^{[1
]}

Wei, Aoqi ^{[1
]}

Yang, Bo ^{[1
]}

Li, Tianjiao ^{[1
]}

Li, Quan ^{[2
]}

Qiu, Di ^{[1
]}

Lu, Kui ^{[2
]}

机构：

[1] Tianjin Normal Univ, Tianjin Key Lab Struct & Performance Funct Mol, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Coll Chem,Minist Educ, Tianjin 300387, Peoples R China

[2] Tianjin Univ Sci & Technol, Coll Biotechnol, Tianjin 300457, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 17期

基金：

美国国家科学基金会;

关键词：

HYPERVALENT IODINE REAGENT; SODIUM TRIFLUOROMETHANESULFINATE; SULFONYL HYDRAZIDES; DIFLUOROMETHYLTHIOLATION; THIOLATION; CHLORIDE; PERFLUOROALKYLTHIOLATION; PYRAZOLONES; INDOLES; ACIDS;

D O I：

10.1021/acs.joc.7b01226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new transition-metal-free route for the direct trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics with CF3SO2Na in the presence of PCl3 was developed. Notably, PCl3 was used as a reducing and chlorination reagent. The transition-metal-free protocol utilized cheap and readily available reagents and exhibited good atom economy; therefore, it will serve as an alternative and practical strategy for the trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics.

引用

页码：9175 / 9181

页数：7

共 36 条

[1] Transition-metal-free direct trifluoromethylthiolation of electron-rich aromatics using CF3SO2Na in the presence of PhPCl2
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[2] Copper-Promoted Trifluoromethylthiolation of Anilines with CF3SO2Na
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[3] Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp2)-H Bonds with CF3SO2Na and RfSO2Na
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14965 - 14969
[4] Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride
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[5] POCl3-Promoted Trifluoromethylthiolation-Based Vicinal Bifunctionalization of Indoles with CF3SO2Na
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (18) : 2078 - 2081
[6] Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides
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Yu, Siqi
Liu, Xiaoqiang
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[7] Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position
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[8] Free-radical promoted bromotrifluoromethylation of arylalkynes with CF3SO2Na and NaBrO3
Shang, Xiao-Jie
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Zhu, Jing
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TETRAHEDRON LETTERS, 2021, 62
[9] External-Oxidant-Free Electrochemical Oxidative Trifluoromethylation of Arenes Using CF3SO2Na as the CF3 Source
Deng, Yong
Lu, Fangling
You, Siqi
Xia, Tianrui
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CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (08) : 817 - 820
[10] Novel Use of CF3SO2Cl for the Metal-Free Electrophilic Trifluoromethylthiolation
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Maeno, Mayaka
Kondo, Hiroya
Shibata, Norio
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ORGANIC LETTERS, 2016, 18 (10) : 2467 - 2470

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