Radical reduction of aromatic azides to amines with triethylsilane

J Org Chem. 2006 Jul 21;71(15):5822-5. doi: 10.1021/jo060824k.

Abstract

Aromatic azides are inert toward triethylsilane under thermal conditions in the presence of a radical initiator, but in the presence of additional catalytic amounts of tert-dodecanethiol, they afford anilinosilanes and thence the corresponding anilines in virtually quantitative yields.