Palladium-Catalyzed Regioselective Carbonylative Coupling/Amination of Aryl Iodides with Unactivated Alkenes: Efficient Synthesis of β-Aminoketones

The carbonylative coupling of aryl halides with unactivated alkenes remains a challenge, because of the low reactivity of acyl-palladium intermediate to the olefins. In this paper, a palladium-catalyzed carbonylative coupling/amination of aryl iodides with unactivated alkenes for the synthesis of β-aminoketone derivatives has been developed. With the assistance of a directing group (8-aminoquinoline, AQ), the coordination of the olefin to acyl-palladium complex can be enhanced, thereby promoting the acylpalladation across the C═C double bonds. A broad range of β-aminoketone derivatives were prepared in moderate to excellent yields with complete regioselectivity by using 4-pentenoic and 2-vinylbenzoic amide derivatives as the starting materials. This methodology involves the formation of two C–C bonds as well as one C–N bond, and provided a method for the carbonylative difunctionalization of unactivated alkenes