Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
Oriol Planas, Vytautas Pečiukėnas, Josep Cornellà
Abstract
Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)–O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.
Topics & Concepts
ChemistryTrifluoromethanesulfonateElectrophileSulfonateBismuthCatalysisLigand (biochemistry)Oxidative coupling of methaneCombinatorial chemistryCatalytic cycleSulfoneCoupling (piping)Medicinal chemistryOrganic chemistrySodiumReceptorMechanical engineeringEngineeringBiochemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques