Make It Green: Copper-Catalyzed Olefin Aziridination in Water with an Iminoiodonane

Abstract

The copper complex Tp(CF3)2,BrCu(NCMe) efficiently catalyses the aziridination of olefins in water using PhI=NTs as the nitrene source, with identical activity than that observed when using dichloromethane as the solvent, under the same experimental conditions. No specific modification of catalyst or substrates are required, nor the presence of additional phase transfer catalyst. Competition experiments and Hammett plots show that the behaviour of the metal centre is the same in both reaction media. This is the first example of a catalytic system employing PhI=NTs for olefin aziridination in water.