RhIII-catalyzed C–H heteroarylation and C–N cleavage: direct access to C2-heteroarylated (NH)-indoles

Abstract

Herein, we disclose 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)-indole and heterocyclic moieties. This catalytic methodology tolerated a diverse range of heterocyclic 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.