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二硫键催化的富电子芳香族化合物碘化反应。

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds.

机构信息

Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Molecular Chirality Research Center (MCRC), and Department of Chemistry, Graduate School of Science , Chiba University , 1-33 Yayoi , Inage, Chiba 263-8522 , Japan.

Nippoh Chemicals Co., Ltd. Neo Kawai Building , 8-15,4-Chome, Nihonbashi-Honchou, Chuo-Ku, Tokyo 103-0023 , Japan.

出版信息

J Org Chem. 2019 Jun 7;84(11):7411-7417. doi: 10.1021/acs.joc.9b00769. Epub 2019 May 17.

Abstract

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

摘要

本文开发了一种二硫代物催化的芳香族化合物亲电碘化反应,使用的是 1,3-二碘-5,5-二甲基海因(DIH)。二硫代物作为路易斯碱激活 DIH,促进了在乙腈中的碘化反应,反应条件温和。该体系适用于广泛的富电子芳香族化合物,包括乙酰苯胺、苯甲醚、咪唑和吡唑衍生物。

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