title: Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I2-Aqueous NH3.
abstract: 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.
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Shohei
authors.initials: S
authors.lastname: Shimokawa
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Yuhsuke
authors.initials: Y
authors.lastname: Kawagoe
authors.affiliation: 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.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Moriyama
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Hideo
authors.initials: H
authors.lastname: Togo