Photoinduced Aminocarbonylation of Aryl Iodides
Takuji Kawamoto1, Aoi Sato1, Ilhyong Ryu2
1Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695.
Abstract:
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.
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