Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols

Abstract

AbstractWe recently reported a general and practical strategy for the Bi(V)-mediated C–H arylation of phenols and naphthols. Our telescoped protocol proceeds via transmetallation from readily available arylboronic acids to a stable Bi(III) precursor, oxidation to a reactive Bi(V) intermediate, and subsequent ortho-selective phenol arylation. The process exhibits broad scope with respect to both components and tolerates functionality that is incompatible with conventional cross-coupling methods. Preliminary investigations provide insight into the mechanism of each key reaction step.1 Introduction2 Design of a Modular and Practical Arylating System3 B-to-Bi Transmetallation: Scope and Mechanism4 Oxidative C–H Arylation: Exemplification and Mechanism5 Conclusionsions