Metal-Free Three-Component Oxyazidation of Alkenes with Trimethylsilyl Azide and <i>N</i>‑Hydroxyphthalimide

A novel and facile oxyazidation of alkenes under metal-free and mild conditions has been reported. A remarkable feature of the developed procedure is consecutive construction of C–O and C–N bonds in one step. The process allows quick and selective assembly of alkyl azide from readily available starting materials, where N-hydroxyphthalimide was used as an oxygen-radical precursor and TMSN3 as the N3 source. A range of aromatic alkenes bearing synthetically useful functional groups was tolerated.