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Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Keisuke Iida*, Shunsuke Ishida, Takamichi Watanabe, Takayoshi Arai*

*Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan, Email: kiidachiba-u.jp, taraifaculty.chiba-u.jp

K. Iida, S. Ishida, T. Watanabe, T. Arai, J. Org. Chem., 2019, 84, 7411-7417.

DOI: 10.1021/acs.joc.9b00769 (free Supporting Information)


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Abstract

In a disulfide-catalyzed electrophilic iodination of electron-rich aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH), 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 substrates, including anisoles, acetanilides, imidazoles, and pyrazoles.

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Key Words

iodination, DIH, organocatalysis


ID: J42-Y2019