Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: A new entry to 1,4-dicarbonyl compounds

Article abstract of DOI:10.1021/ja108754f

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.