Experimental and theoretical study on the cyclic(alkyl)(amino)carbene-copper catalyzed Friedel–Crafts reaction of N,N-dialkylanilines with styrenes

Abstract

The Friedel–Crafts reaction of alkalinous substrates is challenging because of the coordination between amines and traditional acid catalysts. Based on theoretical research, we designed a catalytic process for the Friedel–Crafts reactions of N,N-dialkylanilines in the presence of CAAC-CuCl [CAAC = cyclic(alkyl)(amino)carbene] and KB(C₆F₅)₄. Experimental results show that the catalytic system is suitable for a series of N,N-dialkylanilines and styrenes with good to excellent yields of para-selectivity products. The results are comparable to those obtained in carbene-gold catalyzed processes.