Various methylarenes are treated with 1,3-dibromo-5,5-dimethylhydantoin or N -bromosuccinimide and a catalytic amount of 2,2′-azobis(isobutyronitrile) in acetonitrile, carbon tetrachloride, or methyl tert -butyl ether, and then reacted with benzoic acid, p -toluenethiol, sodium p -toluenesulfinate, aqueous dimethylamine, and succinimide (formed from N -bromosuccinimide) to provide the corresponding arylmethyl benzoates, arylmethyl p -tolyl thioethers, arylmethyl p -tolyl sulfones, N -arylmethyl- N , N -dimethylamines, and N -(arylmethyl)succinimides in good yields, respectively. The reactions involve one-pot, transition-metal-free functionalizations to form C–O, C–S or C–N bonds at the benzylic positions of the methylarenes.
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Togo et al. (2015) studied this question.