An Effective Synthesis of N,N-Diphenyl Carbazolium Salts

Abstract

Tetraaryl ammonium salts are a synthetic challenge, since there is no general method for the arylation of triaryl amines. Contrary to other quaternary ammonium salts, tetraaryl ammonium salts should be very chemically stable. The ipso carbons are not very electrophilic, since the positive charge is distributed throughout the pi systems and they have no acidic β hydrogens. Here we demonstrate a simple approach to N,N-diphenyl carbazolium salts using only three synthetic steps, allowing for an easy production of these salts in large amounts and in a relatively short time. In addition, we study the Cu(I) catalyzed multi-arylation of 2,2’-diaminobiphenyl, focusing on the regioselectivity of each step. Finally, we characterize, for the first time, the solid state structure of a tetraaryl ammonium salt.