Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization

TitleAerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization
Publication TypeJournal Article
Year of Publication2010
AuthorsIzawa, Y, Stahl, SS
JournalAdvanced Synthesis & Catalysis
Volume352
Pagination3223-3229
Date PublishedDec
Accession NumberISI:000285397800022
Keywordsaerobic oxidation, aromatic-compounds, biphenyl, bond activation, C-H activation, Chemistry, Applied, Chemistry, Organic, Complexes, direct arylation, industrial chemistry, mechanism, methyl benzoate, molecular-oxygen, oxidation, oxidative coupling, palladium, palladium(ii) acetate, unactivated arenes
Abstract

An improved method for the direct oxidative coupling of o-xylene could provide streamlined access to an important monomer used in polyimide resins. The use of 2-fluoropyridine as a ligand has been found to enable unprecedented levels of chemo- and regioselectivity in this palladium-catalyzed aerobic oxidative coupling reaction. Preliminary insights have been obtained into the origin of the effectiveness of 2-fluoropyridine as a ligand.