Palladium-Catalyzed Migratory Insertion of Carbenes and C–C Cleavage of Cycloalkanecarboxamides

A palladium catalyzed reaction of cycloalkanecarboxamides and diazomalonates or bis­(phenylsulfonyl)­diazo­methane has been developed. The reaction proceeds via carbene migratory insertion and cascade C–C cleavage pathways. Cycloalkanecarboxamides with four to seven membered rings are applicable in the transformation. A series of ring opening products were prepared with moderate yields. The finding provides valuable clues for the development of new reactions involving carbene migratory insertion and the cleavage of unstrained C­(sp3)–C­(sp3) bonds.