Photoinduced Aminocarbonylation of Aryl Iodides.

Kawamoto, Takuji; Sato, Aoi; Ryu, Ilhyong

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.

ARYL iodides; IODINE compounds; HALIDES; AMINES; ORGANIC compounds

Chemistry - A European Journal, 2015, Vol 21, Issue 42, p14764

0947-6539

Academic Journal

10.1002/chem.201503164