Bromine radical release from a nickel-complex facilitates the activation of alkyl boronic acids: a boron selective Suzuki–Miyaura cross coupling
Monica Oliva, Serena Pillitteri, Johannes Schörgenhumer, Riku Saito, Erik V. Van der Eycken, Upendra K. Sharma
Abstract
a photo-induced homolysis of the Ni-Br bond) and the empty p-orbital on the boron atom. Subsequently, the necessity to tune the BA oxidation potential by means of hydrogen-bonding interaction with solvents or Lewis acid-base type interactions is replaced by a novel halogen radical transfer (XRT) mechanism. The mechanistic hypothesis has been supported by both control experiments and DFT calculations.
Topics & Concepts
AlkylChemistryBoronNickelBromineBoronic acidHalideCoupling (piping)Organic chemistryCombinatorial chemistryPolymer chemistryPhotochemistryMaterials scienceMetallurgyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOrganoboron and organosilicon chemistry