Angelw: Professor Wang Limin and Associate Professor Han Jianwei of East China University of science and technology reported the new development of high valent iodine chemistry in the field of organic synthesis

High valent iodine chemistry has been widely used in organic synthesis, which has attracted the attention of chemists in recent years Recently, under the title of "internal aryl migration of dialyliodonium salts: access to ortho iodo dialyl ethers", applied chemistry of Germany Online reported the research work of Professor Wang Limin and Associate Professor Han Jianwei in the field of organic high valent iodides in the school of chemistry and molecular engineering of East China University of science and technology (angel Chem Int ed., 2018, DOI: 10.1002/anie.201806405 ）。 Diaryl iodonium salt is a kind of trivalent iodine compound Due to its high electron deficiency of iodine positive ion and the easy leaving of iodobenzene, its C (SP 2) - I bond is easier to be activated compared with the general halogenated aromatic hydrocarbon carbon halide bond Therefore, as a unique electrophilic arylation reagent, it has aroused great interest in synthetic chemistry as early as the 1980s In recent years, the emergence of a simple method for the preparation of diaryl iodide has made it one of the new hotspots in organic synthesis Since the beginning of 2011, Professor Wang Limin and Han Jianwei's research team have carried out the research on the arylation of diaryl iodized salt (Asian J org Chem., 2012, 1, 218; angel Chem Int ed., 2012, 51, 10926), and completed the expansion of aromatic co yoke of several aromatic ring parent materials, including the arylation of triarylamine and naphthalimide (synlett, 2013, 24, 1959), 4,5-benzocoumarin (org Lett., 2015, 17, 5654) and benzophenanthrene synthesis (J org Chem., 2018, 83, 49), etc However, up to now, in almost all the reported arylation reactions involving diaryldionium salts, the reaction mode focuses on intermolecular arylation, and with the same amount of iodobenzene as the target product as the by-product, which greatly reduces the atomic economy of the reaction Therefore, how to efficiently utilize two aryl groups in diaryldionium salts has been a difficult problem for chemists A series of novel o-trifluoromethylsulfonate substituted high valent iodide diaryldionium salts were prepared by mild oxidation Under the action of cesium carbonate, the new type of diaryldionium salt can be transferred to o-iododiaryl ethers at room temperature The reaction conditions are mild, the substrate range is wide and the atom utilization rate is high In the process of exploring the mechanism, the author proposed a sulfonyl oriented nucleophilic aromatic substitution pathway In addition, o-iododiaryl ether has been applied to a series of coupling reactions as a universal synthon in organic synthesis Finally, the aryl transfer reaction was successfully applied to the synthesis of 3-iodine-l-thyroxine, which was highly praised by editors and reviewers.