Chen Huangguan, Han Jianwei, Wang Limin
Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12313-12317. doi: 10.1002/anie.201806405. Epub 2018 Aug 23.
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 ) derivative was synthesized by this aryl migration procedure.
通过使用邻位三氟甲磺酸酯取代的二芳基碘鎓盐，开发了一种通过分子内芳基迁移合成邻碘二芳基醚的新方法。反应条件温和，底物范围广泛。机理研究表明这是一条磺酰基导向的亲核芳香取代途径。此外，产物邻碘二芳基醚可作为通用合成子，这在几个偶联反应中得到了证明。此外，通过这种芳基迁移方法合成了一种有用的3-碘-L-甲状腺原氨酸（3-T）衍生物的甲状腺素类似物。
