Direct access to 2-imidazolines from unactivated alkenes

Abstract

The formation of carbon–nitrogen bonds is crucial for the discovery of pharmaceuticals, materials, and agrochemicals. Nitrogen-containing functional groups, especially heterocycles, are common motifs in biologically active compounds. Among these, 2-imidazolines have emerged as important scaffolds with their own class of biological targets. Herein, we report the development of an oxidative amination process to directly convert unactivated alkenes into 2-imidazolines. The combination of ammonia and a commercially available hypervalent iodine reagent achieves the cleavage of the carbon–carbon double bond. Subsequent interception of the resulting imine by ethylenediamine and oxidation furnishes 2-imidazolines in high yields. The reaction is rapid and tolerates a wide range of functional groups, showcasing its potential for late-stage diversification of complex molecules.