TfOH-Promoted C–C Cross-Coupling of Iodonium Ylides with Nucleophiles

Abstract

2-Naphthol and coumarin represent privileged scaffolds prevalent in bioactive agents and chiral catalytic ligands such as naproxen, warfarin, and (R)-(+)-BINOL. Hybridization of these two skeletons is a powerful approach to generate unreported molecular frameworks with unique activity. We herein describe a TfOH-promoted C─C cross-coupling of 2-naphthols and other nucleophiles with coumarin-based iodonium ylides, delivering a series of novel scaffolds. This transformation requires no metal catalysts, proceeding under mild conditions with good functional group tolerance. Gram-scale synthesis and multiple postfunctionalization reactions confirm the synthetic practicability of this methodology. The obtained hybrid molecules exhibit promising potential for further exploration in organic synthesis and drug discovery.