Boron‐Mediated Regioselective Aromatic C−H Functionalization via an Aryl BF<sub>2</sub> Complex
Ganesh Shinde, Henrik Sundén
Abstract
Abstract An efficient regioselective functionalization of 2‐aryl‐heteroarenes and aryl aldehydes via an azaaryl BF 2 complex has been developed. Mechanistically the reaction comprises fluoride to bromide ligand exchange on an aryl boron species and consecutive C−B bond cleavage to deliver a broad range of functionalized products. The reaction is high yielding, has a broad substrate scope where several different heteroarenes can be functionalized with chloro, bromo, iodo, hydroxyl, amine and BF 2 in a highly regioselective fashion. The method can be applied for late‐stage functionalization or for rapid skeleton remodeling with for instance cross‐couplings.
Topics & Concepts
RegioselectivitySurface modificationArylChemistryAmine gas treatingBoronBond cleavageCombinatorial chemistryBromideAromatic amineLigand (biochemistry)Organic chemistryCatalysisBiochemistryReceptorPhysical chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions