Photoinduced Aminocarbonylation of Aryl Iodides.
Transition metal-catalyzed aminocarbonylation of aryl halides with CO and amines, pioneered by Heck and co-workers in the 1970s, is among the most commonly employed reactions to make aromatic amides. A catalyst-free aminocarbonylation of aryl iodides with CO and amines, which simply uses photoirradiation conditions by Xe-lamp, has now been developed. This methodology shows broad functional-group tolerance, including that of heteroaromatic amides. A hybrid radical/ionic chain mechanism, involving electron transfer from zwitterionic radical intermediates generated by nucleophilic attack of amines to aroyl radicals, is proposed.
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695.
Takuji
T
Kawamoto
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695.
Aoi
A
Sato
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695. ryu@c.s.osakafu-u.ac.jp.
Ilhyong
I
Ryu
amides; carbonylation; electron transfer; photochemistry; radical reactions