title: Palladium(II) complexes of readily functionalized bidentate 2-pyridyl-1,2,3-triazole "click" ligands: a synthetic, structural, spectroscopic, and computational study.
abstract: The Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes, the CuAAC "click" reaction is currently receiving considerable attention as a mild, modular method for the generation of functionalized ligand scaffolds. Herein we show that mild one-pot "click" methods can be used to readily and rapidly synthesize a family of functionalized bidentate 2-pyridyl-1,2,3-triazole ligands, containing electrochemically, photochemically, and biologically active functional groups in good to excellent yields (47-94%). The new ligands have been fully characterized by elemental analysis, HR-ESI-MS, IR, (1)H and (13)C NMR and in three cases by X-ray crystallography. Furthermore we have demonstrated that this family of functionalized "click" ligands readily form bis-bidentate Pd(II) complexes. Solution studies, X-ray crystallography, and density functional theory (DFT) calculations indicate that the Pd(II) complexes formed with the 2-(1-R-1H-1,2,3-triazol-4-yl)pyridine series of ligands are more stable than those formed with the [4-R-1H-1,2,3-triazol-1-yl)methyl]pyridine "click" ligands.
authors.affiliation: Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand.
authors.forename: Kelly J
authors.initials: KJ
authors.lastname: Kilpin
authors.forename: Emma L
authors.initials: EL
authors.lastname: Gavey
authors.forename: C John
authors.initials: CJ
authors.lastname: McAdam
authors.forename: Christopher B
authors.initials: CB
authors.lastname: Anderson
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Lind
authors.forename: Courtney C
authors.initials: CC
authors.lastname: Keep
authors.forename: Keith C
authors.initials: KC
authors.lastname: Gordon
authors.forename: James D
authors.initials: JD
authors.lastname: Crowley
mesh_terms: D057930:Click Chemistry; D018360:Crystallography, X-Ray; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D008024:Ligands; D009942:Organometallic Compounds; D014230:Triazoles; D010165:Palladium