Synthesis and Characterization of Post-β-Carbon-Elimination Organopalladium Complexes
Taeho Kang, Yue Fu, Rei Matsuura, Anna L. Liu, Tanner C. Jankins, Arnold L. Rheingold, Jake Bailey, Milan Gembický, Peng Liu, Keary M. Engle
Abstract
A unique family of N,N,π,C-palladacycles are synthesized from 8-aminoquinoline-coupled nopol derivatives through directed 1,2-migratory insertion of in situ generated arylpalladium(II) species followed by β-carbon elimination. These palladacycles have exceptional stability under air and moisture at room temperature, enabling successful isolation and characterization by X-ray crystallography, NMR, and high-resolution mass spectrometry. Computational studies shed light on the facile β-alkyl elimination step and the origins of the high stability of these post-β-carbon-elimination complexes.
Topics & Concepts
OrganopalladiumChemistryCarbon fibersAlkylOxidative additionCharacterization (materials science)Reductive eliminationElimination reactionMass spectrometryCombinatorial chemistryOrganic chemistryStereochemistryNanotechnologyCatalysisPalladiumChromatographyMaterials scienceComposite numberComposite materialCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms