Combined experimental/theoretical study of d-glucosamine promoted Ullmann-type C–N coupling catalyzed by copper(i): does amino really count?

Abstract

Ullmann type C–N coupling reaction catalyzed by copper(I) with D-glucosamine derivatives as promoters was studied by means of combined experimental/theoretical investigation. The catalytic role of D-glucosamine was addressed. In contrast with previous speculations, the amino group may not count in the catalytic cycle in which the oxidative addition/reductive elimination mechanism works. Experimental results are in good agreement with theoretical findings. Extensive work indicates the wide applicability of the C–N coupling strategy exploited in this work.