Pd(II)-Catalyzed Carbonylation of C(sp3)−H Bonds: A New Entry to 1,4-Dicarbonyl Compounds

Abstract
Pd(II)-catalyzed β-C(sp3)−H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp3)−H cleavage and insertion of CO into the resulting [Pd(II)−C(sp3)] bond, intramolecular C−N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp3)−H carbonylation of cyclopropanes.