N-methylanilines from benzylic azides

Article abstract of DOI:10.1016/S0040-4039(99)00148-3

Benzylic azides are converted into N-methylanilines efficiently in the presence of a Bronsted or Lewis acid and Et₃SiH. The combination of SnCl₄/Et₃SiH and 4-n-butylbenzyl azide appears to form an aminodiazonium trichlorostannate(II), which undergoes the rearrangement to an iminium salt that is then reduced to N-methyl-4-n-butylaniline by Et₃SiH.