Iron-catalyzed ligand-free diazidation of alkenes controlled by the ratio of TBHP to TMSN3

Abstract

The diazidation of alkenes through an iron-catalyzed, ligand-free system has been established, providing straightforward access to structurally vicinal diazides in good yields at room temperature with TMSN₃ as the azido source. The ratio of ^tBuOOH to TMSN₃ was essential for the reaction: one equivalent TMSN₃ was needed to react with ^tBuOOH to form HN₃ as a nucleophile in the reaction ultimately achieving the diazidation of alkenes.