Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho‐Iodo Diaryl Ethers |
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| Authors: | Huangguan Chen Prof?Dr Jianwei Han Prof?Dr Limin Wang |
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| Institution: | 1. Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, China;2. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, Shanghai, China |
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| Abstract: | 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‐T1) derivative was synthesized by this aryl migration procedure. |
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| Keywords: | arylation ethers hypervalent compounds reaction mechanisms synthetic methods |
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