Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents

被引：14

作者：

Zhao, Xia ^{[1
]}

Wei, Aoqi ^{[1
]}

Lu, Xiaoyu ^{[1
]}

Lu, Kui ^{[2
]}

机构：

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

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

来源：

MOLECULES | 2017年 / 22卷 / 08期

基金：

美国国家科学基金会;

关键词：

thiolation; oxindole; sulfonyl chloride; tetrabutylammonium iodide; triphenylphosphine; ELECTRON-RICH AROMATICS; TRIFLUOROMETHANESULFONYL CHLORIDE; DIFLUOROMETHANESULFONYL CHLORIDE; 3-SUBSTITUTED OXINDOLES; ARYLSULFONYL CHLORIDES; HYDRAZIDES; TRIFLUOROMETHYLTHIOLATION; DIFLUOROMETHYLTHIOLATION; PHYTOALEXINS; PYRAZOLONES;

D O I：

10.3390/molecules22081208

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

3-Sulfanyloxindoles were synthesised by triphenylphosphine-mediated transition-metal-free thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents. The above reaction was promoted by iodide anions, which was ascribed to the in situ conversion of sulfenyl chlorides into the more reactive sulfenyl iodides. Moreover, the thiolation of 3-aryloxindoles was facilitated by bases. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions make this protocol more practical for preparing 3-sulfanyloxindoles than traditional methods.

引用

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