Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)]2 catalyzes the aza-Friedel–Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp3 C–N bond and elimination of 1,3,5-trimethoxybenzene.