Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylations of Azoles with Allylic Alcohols
Matthew T. Zambri, Teh Ren Hou, Mark S. Taylor
Abstract
A method for regioselective palladium-catalyzed allylic alkylation of ambident nitrogen heterocycles, employing simple allylic alcohols as electrophile precursors, is described. An organoboron co-catalyst serves both to activate the azole-type nucleophile toward selective N-functionalization and to accelerate the formation of a π-allylpalladium complex from the allylic alcohol. The method can be applied to various heterocycle types, including 1,2,3- and 1,2,4-triazoles, tetrazoles, pyrazoles, and purines, and can be extended to substituted allylic alcohol partners.
Topics & Concepts
ChemistryRegioselectivityAllylic rearrangementElectrophileNucleophileTsuji–Trost reactionPalladiumCatalysisOrganoboron compoundsAlcoholOrganic chemistryAzoleCombinatorial chemistryMedicinal chemistryAntifungalDermatologyMedicineChemical Synthesis and AnalysisCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods