Copper(I) catalysis: Synthesis of N,N′-diarylated and N-aryl,N′-formylated chiral C < inf > 2 < /inf > -symmetric diamines

Abstract

Chiral N,N′-diaryl C2-symmetric diamines and N-aryl,N′-formyl-trans-(1R,2R)-diaminocyclohexane are readily accessed by copper catalyzed N,N′-diarylation and N-aryl,N′-formylation of trans-(1R,2R)-diaminocyclohexane with aryl bromides. N,N′-diarylation using (R)-1,1′-binaphthyl-2,2′-diamine and iodobenzene gave the corresponding (R)-N,N′-diphenyl-1,1′-binaphthyl-2,2′-diamine derivative in 83% yield. © 2009 Elsevier B.V. All rights reserved.