Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions  

作　　者：Xiao-Chun Yu Bo Li Bao-Hua Yu Qing Xu 

机构地区：[1]College of Chemistry and Materials Engineering,Wenzhou University

出　　处：《Chinese Chemical Letters》2013年第7期605-608,共4页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China(No.20902070);Natural Science Foundation of Zhejiang Province(No.Y4100579);Qianjiang Talents Program of Zhejiang Province(No.QJD0902004) for financial supports

摘　　要：Tetrabutylammonium fluoride （TBAF） effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane （PhSTMS） under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution （SNAr） mechanism.Tetrabutylammonium fluoride （TBAF） effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane （PhSTMS） under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution （SNAr） mechanism.

关 键 词：Phenylthiotrimethylsilane Nitroarenes Denitrative substitution Unsymmetrical diaryl thioethers Nucleophilic aromatic substitution 

分 类 号：O621.25[理学—有机化学]