Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates
Luke O’Brien, Stephen P. Argent, Kristaps Ermanis, Hon Wai Lam
Abstract
Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Evidence suggests that the reactions proceed through nucleophilic allylgold(I) intermediates formed by transmetalation from allylboronates. Density functional theory (DFT) calculations provided mechanistic insight.
Topics & Concepts
NucleophilePyridiniumChemistryTransmetalationCatalysisIonDensity functional theoryNucleophilic additionCombinatorial chemistryMedicinal chemistryComputational chemistryOrganic chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms