Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis

The efficient selective oxidation and functionalization of CH bonds with molecular oxygen and a copper catalyst to prepare the corresponding ketones was achieved with ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process. The N‐heterocyclic compounds and ethyl chloroacetate work synergistically to activate CH bonds in the methylene group, which results in the easy generation of free radical intermediates, thus leading to the corresponding ketones in good yields. Molecular oxygen can be used for the selective oxidation of CH bonds of N‐heterocyclic compounds to the corresponding ketones with a copper catalyst and ethyl chloroacetate as a promoter. In this transformation, various substituted N‐heterocyclic compounds were well tolerated. Preliminary mechanistic investigations indicated that organic radical species were involved in the overall process.