Selective Conversion of Benzylic C-H Bonds to an Amine Function by Oxidative Nucleophilic Substitution

Article abstract of DOI:10.1055/s-1988-27747

The benzylic proton of alkylarenes 1 was replaced by an azido group in one step by reaction with trimethylsilyl azide or hydrazoic acid in chloroform in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).The 1-arylalkyl azides 2 were reduced to amines 3, which were characterized as their hydrochlorides 4.