Elemental Sulfur-Mediated Aromatic Halogenation

Junpei Matsuoka, Yuna Yano, Yuuka Hirose, Koushi Mashiba, Nanako Sawada, Akira Nakamura, Tomohiro Maegawa*

*School of Pharmaceutical Sciences, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan, Email: maegawaphar.kindai.ac.jp

J. Matsuoka, Y. Yano, Y. Hirose, K. Mashiba, N. Sawada, A. Nakamura, T. Maegawa, J. Org. Chem., 2024, 89, 770-777.

DOI: 10.1021/acs.joc.3c02259

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Abstract

Elemental sulfur (S₈) mediates aromatic halogenations using N-halosuccinimides for bromination and chlorination or 1,3-diiodo-5,5-dimethylhydantoin for iodination. The reaction effectively halogenated also less-reactive aromatic compounds, such as ester-, cyano-, and nitro-substituted anisole derivatives.

see article for more examples

proposed mechanism

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Key Words

bromination, chlorination, iodination, NBS, NCS, DIH

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ID: J42-Y2024