Cu(OTf)2-Catalyzed Access to 2,4,5-Trisubstituted Imidazoles from Acyclic Reissert Compounds

Abstract

A Cu(OTf)₂-catalyzed cascade self-coupling of N-acyl-α-aminonitriles (acyclic Reissert compounds) has been developed to afford 2,4,5-trisubstituted imidazoles in moderate to good yields. Single-crystal X-ray diffraction confirmed the structure of a representative 1H-2,4-disubstituted-5-acylimidazole, while NMR studies revealed N1/N3 tautomerism in selected cases. The synthetic utility of this protocol was further demonstrated by gram-scale synthesis and carbonyl reduction.