Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I₂-Aqueous NH₃

Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama and Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

S. Shimokawa, Y. Kawagoe, K. Moriyama, H. Togo, Org. Lett., 2016, 18, 784-787.

DOI: 10.1021/acs.orglett.6b00048

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Abstract

Various ethylarenes were converted into the corresponding primary aromatic amides in good yields using N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) followed by reaction with molecular iodine and aq NH₃ in one pot. It was found that aryl α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and a iodoform-type reaction occurred at the second reaction step.

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Key Words

Iodoform Reaction, Oxidative Amidation, NBS, I₂

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ID: J54-Y2016