文献类型：期刊文献

英文题名：Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers

作者：Chen, Huangguan[1];Han, Jianwei[1,2];Wang, Limin[1]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China

年份：2018

卷号：57

期号：38

起止页码：12313

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20183605779059);WOS:【SCI-EXPANDED(收录号:WOS:000444225100014)，CCR-EXPANDED(收录号:WOS:000444225100014)】；

基金：The work was supported by the National Nature Science Foundation of China (NSFC 21472213, 21772039), the National Key Research and Development Program (2016YFA0200302), as well as by the Croucher Foundation (Hong Kong) in the form of a CAS-Croucher Foundation Joint Laboratory Grant, the Fundamental Research Funds for the Central Universities and the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.

语种：英文

外文关键词：arylation; ethers; hypervalent compounds; reaction mechanisms; synthetic methods

摘要：By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-L-thyronine (3-T-1) derivative was synthesized by this aryl migration procedure.