RhIII-Catalyzed C–H Heteroarylation and C–N Cleavage: Direct Access to C2-heteroarylated (NH)-indoles

Abstract

Herein, we disclosed a Cp*Rh(III)-catalyzed C2-heteroarylation of indoles bearing an N 2,6 difluoroaryl amide auxiliary with heterocyclic boronates, followed by auxiliary cleavage, offering an efficient route to biheteroaryl derivatives containing (NH)-indoles and heterocycles moieties. This catalytic methodology tolerated a diversity of heterocycles boronates and indoles well. Successful late-stage modification of the antimigraine drug sumatriptan further highlights its potential utility in the preparation of indole-based pharmaceutical molecules.