Transition-metal-free trifluoromethylthiolation and difluoromethylthiolation of thiols with trifluoromethanesulfonyl chloride and difluoromethanesulfonyl chloride

被引：31

作者：

Zhao, Xia ^{[1
]}

Li, Tianjiao ^{[1
]}

Yang, Bo ^{[1
]}

Qiu, Di ^{[1
]}

Lu, Kui ^{[2
]}

机构：

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

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

来源：

TETRAHEDRON | 2017年 / 73卷 / 22期

基金：

美国国家科学基金会;

关键词：

Thrifluoromethylthiolation; Difluoromethylthiolation; Thiol; Trifluoromethanesulfonyl chloride; Difluoromethanesulfonyl chloride; ALPHA-FLUORINATED ETHERS; ARYL SULFONYL HYDRAZIDES; ELECTRON-RICH AROMATICS; SULFENYLATION REAGENTS; THIOETHERS; THIOLATION; AMINES; THIOLSULFONATES; PYRAZOLONES; SULFIDES;

D O I：

10.1016/j.tet.2017.04.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triphenylphosphine-mediated metal-free trifluoromethylthiolation and difluoromethylthiolation of thiols by CF3SO2Cl and CHF2SO2Cl to synthesize trifluoromethyl disulfides and difluoromethyl disulfides, respectively, was achieved at room temperature. Iodine generated in situ from iodide facilitated this reaction via the formation of iodotriphenylphosphonium iodide which could serve as a reducing agent in this transformation. Readily available reagents and mild reaction conditions without transition-metals allow this protocol to be more practical than traditional methods. (C) 2017 Published by Elsevier Ltd.

引用

页码：3112 / 3117

页数：6

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