Transition-metal-free azide insertion of N -triftosylhydrazones using a non-metallic azide source.

Benzylic azides, an important class of active organic synthons, were synthesized in high yields from the easily accessible N -triftosylhydrazones with stable TMSN 3 under mild conditions. The reaction features high efficiency and excellent functional group tolerance, as illustrated by gram-scale synthesis and the synthesis of drug-like molecules. Mechanistic studies reveal that azidation occurs at the electron-deficient diazo-carbon via the elimination of N 2 by an azide ion.