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

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• 作者：Shohei Shimokawa ; Yuhsuke Kawagoe ; Katsuhiko Moriyama ; Hideo Togo
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：784-787
• 全文大小：329K
• ISSN：1523-7052

文摘

A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, 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 their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes.