Iridium(iii)- and rhodium(iii)-catalyzed coupling of anilines with α-diazoesters via chelation-assisted C–H activation

Abstract

Iridium and rhodium complexes exhibited complementary activity in the coupling of N-functionalized anilines with α-diazoesters via C–H activation. The coupling with α-diazo β-ketoesters was realized under Ir(III) catalysis to afford ester-functionalized indoles. In contrast, coupling with α-diazomalonates under Rh(III) catalysis afforded alkylation products without any annulation. Mechanistic studies have been performed and an iridacycle has been isolated as an intermediate.