ArticleInorganic chemistry2012
Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.
Article in Inorganic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed, 131 citations in OpenAlex.
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- The Chlorido-Bismuth Dication: A Potent Lewis Acid Captured in a Hepta-Coordinate Species with a Stereochemically Active Lone Pair.Inorganic chemistry · 2024Article
- Competing Mechanisms in Palladium-Catalyzed Alkoxycarbonylation of Styrene.ACS catalysis · 2024Article
- Computer vision for non-contact monitoring of catalyst degradation and product formation kinetics.Chemical science · 2023Article
- Solvent coordination to palladium can invert the selectivity of oxidative addition.Chemical science · 2022Article
- Solvothermal Synthesis of [CrChemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.Chemical science · 2020Article
- Critical Role of Anions in Platinum(II) Precursors upon the Structural Motifs of Six-Membered CycloplatinatedACS omega · 2018Article
- Single operation palladium catalysed C(spChemical science · 2017Article
- Mechanism of the CuChemical science · 2016Article
- The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.Chemical science · 2014Article
- Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.Angewandte Chemie (International ed. in English) · 2013Article
- Aerobic dehydrogenation of cyclohexanone to cyclohexenone catalyzed by Pd(DMSO)2(TFA)2: evidence for ligand-controlled chemoselectivity.Journal of the American Chemical Society · 2013Article
- Mild aromatic palladium-catalyzed protodecarboxylation: kinetic assessment of the decarboxylative palladation and the protodepalladation steps.The Journal of organic chemistry · 2013Article
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4 authors at 1 institution in 1 country.
Funding
Abstract
Recent studies have shown that Pd(DMSO)(2)(TFA)(2) (TFA = trifluoroacetate) is an effective catalyst for a number of different aerobic oxidation reactions. Here, we provide insights into the coordination of DMSO to palladium(II) in both the solid state and in solution. A crystal structure of Pd(DMSO)(2)(TFA)(2) confirms that the solid-state structure of this species has one O-bound and one S-bound DMSO ligand, and a crystallographically characterized mono-DMSO complex, trans-Pd(DMSO)(OH(2))(TFA)(2), exhibits an S-bound DMSO ligand. (1)H and (19)F NMR spectroscopic studies show that, in EtOAc and THF-d(8), Pd(DMSO)(2)(TFA)(2) consists of an equilibrium mixture of Pd(S-DMSO)(O-DMSO)(TFA)(2) and Pd(S-DMSO)(2)(TFA)(2). The O-bound DMSO is determined to be more labile than the S-bound DMSO ligand, and both DMSO ligands are more labile in THF relative to EtOAc as the solvent. DMSO coordination to Pd(II) is substantially less favorable when the TFA ligands are replaced with acetate. An analogous carboxylate ligand effect is observed in the coordination of the bidentate sulfoxide ligand, 1,2-bis(phenylsulfinyl)ethane to Pd(II). DMSO coordination to Pd(TFA)(2) is shown to be incomplete in AcOH-d(4) and toluene-d(8), resulting in Pd(II)/DMSO adducts with <2:1 DMSO/Pd(II) stoichiometry. Collectively, these results provide useful insights into the coordination properties of DMSO to Pd(II) under catalytically relevant conditions.
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