Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
Carolin Gerleve, Armido Studer
Abstract
Abstract Readily prepared tetraarylborates undergo selective (cross)‐coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO 2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO 2 /O 2 without any additional nitroxide‐based cocatalyst. Transition‐metal‐free catalytic oxidative ligand cross‐coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.
Topics & Concepts
Transition metalOxidative phosphorylationOxidative coupling of methaneCoupling (piping)ChemistryPhotochemistryMaterials scienceOrganic chemistryCatalysisMetallurgyBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAxial and Atropisomeric Chirality Synthesis