Catalytic ring-closing reactions of gold compounds containing bis(phosphino)ferrocene ligands

Michaels, Toni A.; Pritchard, Olivia F.; Dell, Justine S.; Bezpalko, Mark W.; Kassel, W. Scott; Nataro, Chip

doi:10.1016/j.jorganchem.2019.03.006

Cited by 10 publications

(5 citation statements)

References 92 publications

(20 reference statements)

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“…The FcH was sublimed prior to use in electrochemical experiments. The [(AuCl) 2 (μ-PP)] (PP = dppf, 39 dippf, 44 dcpf, 45 dtbpf, 46 dppdtbpf, 47 dfurpf, 48 and (dppc + ) 43 ) compounds, Na[BArF 24 ], 43 dppc + , 81 dppr, 34 and dppo 35 were prepared according to literature procedures. All NMR spectra were obtained in CDCl 3 using a Bruker Avance III HD 400 FT-NMR.…”

Section: Methodsmentioning

confidence: 99%

“…35 This reaction proceeds through the gold assisted interaction of the alkyne and alcohol groups present on the starting material. 48 This study highlighted the enhanced catalytic activity [(AuCl) 2 (μ-PP)] compounds in the presence of Na[BArF 24 ]. Similarly, the catalytic activity of [(AuCl) 2 (μ-PP)] compounds in the hydroamination of phenylacetylene with various aryl amines was significantly enhanced by the addition of Na[BArF 24 ].…”

Section: Introductionmentioning

confidence: 91%

“…[31][32][33]37,38 In recent years the study of gold catalysts containing these ligands has grown in interest due to their ability to activate unsaturated carbon-carbon bonds in cross-coupling reactions. 39 The synthesis of various gold(I) [(AuCl) 2 (μ-PP)] (PP = 1,1′-bis( phos-phino)metallocene) compounds have been reported [39][40][41][42][43][44][45][46][47][48] and their catalytic properties have been evaluated for several organic reactions, including hydroamination and a variety of ring closing reactions. [48][49][50][51] More recently, gold catalysts have been studied in conjunction with halide abstracting agents such as AgSbF 6 , AgNTf 2 , and AgOTf.…”

Section: Introductionmentioning

confidence: 99%

“…39 The synthesis of various gold(I) [(AuCl) 2 (μ-PP)] (PP = 1,1′-bis( phos-phino)metallocene) compounds have been reported [39][40][41][42][43][44][45][46][47][48] and their catalytic properties have been evaluated for several organic reactions, including hydroamination and a variety of ring closing reactions. [48][49][50][51] More recently, gold catalysts have been studied in conjunction with halide abstracting agents such as AgSbF 6 , AgNTf 2 , and AgOTf. [52][53][54] In 2020, Tsurusaki examined the effectiveness of these additives in the presence of a variety of diphosphine-gold(I) complexes in an intramolecular alkyne hydroarylation of a phenol-derivative.…”

Section: Introductionmentioning

confidence: 99%

“…35 This reaction proceeds through the gold assisted interaction of the alkyne and alcohol groups present on the starting material. 48…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]

et al. 2022

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…35 This reaction proceeds through the gold assisted interaction of the alkyne and alcohol groups present on the starting material. 48…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]

et al. 2022

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O‐Alkyldithiophosphate Nickel Complexes with dcpf Ligand as Efficient Electrocatalysts for Hydrogen Evolution

Zhang

Deng

Xie

et al. 2019

Applied Organom Chemis

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Six new O‐alkyldithiophosphate nickel complexes with dcpf ligand, [(dcpf)Ni(S2P{O}OR)] (dcpf = 1,1′‐bis (dicyclohexylphosphino)ferrocene, R = CH3 (1), CH3CH2 (2), Ph (3), 4‐MeC6H4 (4), PhCH2 (5) and PhCH2CH2 (6)), have been synthesized by the treatment of dcpf with ((RO)2PS2)2Ni in satisfactory yields. These complexes were characterized by elemental analysis, spectroscopy (FTIR, UV–vis, 1H, 13C, and 31P NMR), thermogravimetric analysis and single crystal X‐ray diffraction. The nickel atom in 1, 2·CH2Cl2, 3·CH2Cl2, 4·2CH2Cl2·THF, and 2(5)·hexane adopts a slightly distorted square‐planar coordination environment finished by two phosphorus atoms of dcpf ligand and two sulfur atoms of O‐alkyldithiophosphate ligand. Furthermore, the electrochemical properties for complexes 1–6 were also investigated by cyclic voltammetry. With the addition of 120 mM trifluoroacetic acid (TFA), the turnover frequency (TOF) values for 1–6 are estimated to be 1243.83, 1046.54, 1331.71, 2545.29, 1899.03, and 1191.37 s−1, with the overpotential (η) values of 0.62, 0.58, 0.71, 0.67, 0.60, and 0.56 V, respectively. The result of electrochemical studies indicates that all complexes can be used as efficient molecular eletrocatalysts for the reduction of protons to hydrogen in the presence of TFA in MeCN.

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Ferrocenyl Dinuclear Gold(I) Complexes. Study of their Structural Features and the Influence of Bridging and Phosphane Ligands in a Catalytic Cyclization Reaction

Pérez‐Sánchez,

Herrera,

Concepción Gimeno

2024

Chemistry A European J

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The combination of the ferrocene moiety with gold(I) catalysis remains a relatively unexplored field. In this article, we delve into the synthesis, characterization, and potential catalytic activity of four complexes utilizing both monodentate and bidentate ferrocenyl diphenylphosphane ligands (ppf and dppf), coordinated with two gold(I) metal centers, linked by either chloride or pentafluorophenylthiolate bridging ligands. This leads to the formation of cationic "self‐activated" precatalysts capable of initiating the catalytic cycle without the need for external additives. The catalytic activity of these complexes was assessed through a model reaction in gold(I) catalysis, specifically the cyclization of a N‐propargylbenzamide to produce an oxazole. In addition, we studied and compared the influence exerted by both the phosphane and the bridging ligand on the performance of these catalysts.

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Catalytic ring-closing reactions of gold compounds containing bis(phosphino)ferrocene ligands

Cited by 10 publications

References 92 publications

Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]

Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]

O‐Alkyldithiophosphate Nickel Complexes with dcpf Ligand as Efficient Electrocatalysts for Hydrogen Evolution

Ferrocenyl Dinuclear Gold(I) Complexes. Study of their Structural Features and the Influence of Bridging and Phosphane Ligands in a Catalytic Cyclization Reaction

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Catalytic ring-closing reactions of gold compounds containing bis(phosphino)ferrocene ligands

Cited by 10 publications

References 92 publications

Synthesis of disubstituted furans catalysed by [(AuCl)2(μ-bis(phosphino)metallocene)] and Na[BArF24]

Synthesis of disubstituted furans catalysed by [(AuCl)2(μ-bis(phosphino)metallocene)] and Na[BArF24]

O‐Alkyldithiophosphate Nickel Complexes with dcpf Ligand as Efficient Electrocatalysts for Hydrogen Evolution

Ferrocenyl Dinuclear Gold(I) Complexes. Study of their Structural Features and the Influence of Bridging and Phosphane Ligands in a Catalytic Cyclization Reaction

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Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]

Synthesis of disubstituted furans catalysed by [(AuCl)₂(μ-bis(phosphino)metallocene)] and Na[BArF₂₄]