Synthesis of N-H Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acid

Hydroxylamine-O-sulfonic acid (1) is an inexpensive nitro-free amination reagent with superior thermal stability, and is used for the synthesis of N-H aziridines from alkenes. Under basic conditions at room temperature, 1 reacts with unactivated olefins with a catalytic amount of Rh₂(esp)₂ to afford N-H aziridines. The synthetic method using 1 is tolerant towards oxygen and trace moisture. Additionally, this reaction can be safely conducted on large scale.