| Imides are prevalent organic structures in various pharmaceuticals and agrochemicals, and also widely applied in high-strength or electrically conductive materials.Tertiary aryl amides also are ubiquitous in a variety of biologically active molecules, pharmaceuticals, and polymers. Conventionally, these compounds are typically synthesized by acylation of amines/amides with carboxylic acids or acid chlorides. However, the extensive application of these highly toxic reagents always produce large amounts of toxic waste materials make serious environmental problems and equipment corrosion. Therefore, to avoid highly hazardous reagents and improve atom economy, many synthetic routes have been developed as alternative methods for the synthesis of imides and tertiary benzanilides.Over the past decades, significant efforts have been devoted to the development of transition metal catalyzed cross-coupling reactions, which have been considered the most powerful tool for the construction of C-C or C-heteroatom bond frameworks. Among them, the palladium-catalyzed aminocarbonylation has attracted considerable attention as powerful method for the construction of amides. However, the previous methods for the aminocarbonylation of aryl halides used strong nucleophilic reagents (aliphatic amines/primary aromatic amines) as the partners, and need expensive bulky phosphine ligands, high pressure temperature and specialized high-pressure reaction vessels. Therefore, the efforts to find new catalytic systems for carbonylation of weak nucleophilic amides and bulky anilines under mild conditions are still highly desirable. In this paper, the synthesis methods to afford imides and amides have been summarized. Then, a novel and efficient access to imides and tertiary benzanilides through palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been achieved by reagent control under mild reaction conditions. |
PDF Full Text Request