期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 38, 页码 12313-12317出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806405
关键词
arylation; ethers; hypervalent compounds; reaction mechanisms; synthetic methods
资金
- National Nature Science Foundation of China (NSFC) [21472213, 21772039]
- National Key Research and Development Program [2016YFA0200302]
- Croucher Foundation (Hong Kong) in the form of a CAS-Croucher Foundation Joint Laboratory Grant
- Fundamental Research Funds for the Central Universities
- Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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.
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