Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 42, Pages 14764-14767Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503164
Keywords
amides; carbonylation; electron transfer; photochemistry; radical reactions
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Funding
- Grants-in-Aid for Scientific Research [26248031, 15H05850] Funding Source: KAKEN
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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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