Chemoselective three-component synthesis of homoallylic azides using an FeCl3 catalyst

Abstract

A one-pot, three-component synthesis of homoallylic azides from corresponding aldehydes, TMS-allyl, and TMS-N₃ has been developed for the first time using an FeCl₃ catalyst. The aromatic and hetero-aromatic aldehydes provided the corresponding homoallylic azides with excellent chemoselectivity. This direct azido-allylation process is also readily scalable (1–28 mmol). The mechanism of the process is proposed. Finally, the selective as well as simultaneous functionalization of homoallylic azides has also been exemplified.