Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 2, Pages 594-597Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo016076a
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Aroyl imides were prepared by a palladium-catalyzed aminocarbonylation reaction of aryl bromides with carbon monoxide and primary amides in good yields (58-72%). The reactions were carried out under mild conditions (5 bar, 120 degreesC) using 1 mol % of a palladium phosphine complex. Several aryl bromides were reacted with formamide, acetamide, benzamide, and benzenesulfonamide, respectively. For activated aryl bromides, a phosphine-to-palladium ratio of 2:1 was sufficient, but less reactive aryl bromides required a ligand-to-palladium ratio of 6:1 in order to stabilize the catalyst and achieve full conversion. The imides were very sensitive to aqueous basic conditions and were easily converted to aroyl amides or benzoic acids.
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