Carbon-Heteroatom Bond Formation at the Benzylic Position of Methylarenes

Togo et al. have reported the one-pot C–heteroatom bond formation from the C–H bond at the benzylic position of methylarenes. They show the reaction pathway as follows. Initially, the reaction proceeds through Wohl–Ziegler bromination of methylarenes with 1,3-dibromo-5,5-dimethylhydantoin or NBS, and AIBN as a radical initiator, followed by reactions with different nucleophiles. Most of the C–heteroatom bond formation methods require toxic transition metals at high temperature, and the reactions are limited mainly to the C–O bond formation. In contrast, this reaction proceeds under mild transition metal-free conditions. This method is useful for the synthesis of functionalized methylarenes.