Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
Molecular Chirality Research Center, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
Org Lett. 2016 Feb 19;18(4):784-7. doi: 10.1021/acs.orglett.6b00048. Epub 2016 Jan 27.
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.
通过在乙酸乙酯和水、乙腈和水或氯仿和水的混合物中，用催化量的 2,2'-偶氮双（异丁腈）处理，将各种乙苯转化为相应的伯芳酰胺，产率良好。随后，一锅法用分子碘和氨的水溶液进行反应。研究发现，在第一步反应中形成了芳基α-溴甲基酮和/或芳基甲基酮，在第二步反应中发生了碘仿型反应，从而得到伯芳酰胺。该反应是一种从乙苯制备伯芳酰胺的有用且实用的无过渡金属方法。
