Dichloro Bis(acetonitrile) Palladium

Carretero, Juan C.; Arrayás, Ramón Goméz

doi:10.1002/047084289x.rn00908

Cited by 9 publications

(7 citation statements)

References 208 publications

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“…1‐Methyl‐1‐phenylhydrazine and 2‐hydrazinylpyridine were obtained from TCI Deutschland GmbH and used as received. Dichloridobis(acetonitrile)palladium(II), [40] dichlorido(1,5‐cyclooctadiene)platinum(II) [41] and [PdCl 2 ( PCHO‐ κ P )] 2 [30] were synthesised according to the literature. NMR spectra were recorded on a Bruker Avance III HD 400 MHz NMR spectrometer at 25 °C ( 1 H 400.13 MHz, 13 C 100.63 MHz, 19 F 376.53 MHz and 31 P 162.02 MHz).…”

Section: Methodsmentioning

confidence: 99%

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

et al. 2023

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Phosphino hydrazones represent a versatile class of nitrogen‐containing phosphine ligands. Herein, we report a modular synthesis of phosphino hydrazone ligands by hydrazone condensation reaction of three different aryl hydrazines with 3‐(diphenylphosphino)propanal (PCHO). Complexation reactions of these phosphino hydrazone ligands with palladium(II) and platinum(II) were investigated and the catalytic activity of the palladium(II) complexes was explored in a Cu‐free Sonogashira cross‐coupling reaction achieving yields up to 96 %. Additionally it was shown that the catalytically active species is homogeneous.

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Section: Methodsmentioning

confidence: 99%

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

et al. 2023

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“…Ligands 1 – 3 were prepared as outlined in previous work [ 31 ]. [Pd(CH 3 CN) 2 Cl 2 ] was prepared according to a published procedure [ 60 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

et al. 2021

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The aqueous synthesis of Pd(II) complexes with alkylated tripeptides led to the hydrolysis of the peptides at low pH values and mixtures of complexed peptides were formed. A non-aqueous synthetic route allowed the formation and isolation of single products and their characterization. Pd(II) complexes with α-Asp(OR)AlaGly(OR), β-Asp(OR)AlaGly(OR), and TrpAlaGly(OR) (R = H or alkyl) as tri and tetradentate chelates were characterized. The tridentate coordination mode was accompanied by a fourth monodentate ligand that was shown to participate in both ligand exchange reactions and a direct removal to form the tetradentate coordination mode. The tetradentate coordination revealed a rare a hemi labile carbonyl goup coordination mode to Pd(II). Reactivity with small molecules such as ethylene, acids, formate, and episulfide was investigated. Under acidic conditions and in the presence of ethylene; acetaldehyde was formed. The Pd(II) is a soft Lewis acid and thiophilic and the complexes abstract sulfur from episulfide at apparent modest catalytic rates. The complexes adopt a square planar geometry according to a spectroscopic analysis and DFT calculations that were employed to evaluate the most energetically favorable coordination geometry and compared with the observed infrared and NMR data.

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“…In pursuit of experimental optimization, the catalytic system using PdCl 2 (MeCN) 2 [46], previously identified as highly efficient in preliminary trials, was employed to construct a partial factorial DoE [42][43][44]47]. This optimization focused on investigating both the selectivity toward n-decanal and the conversion of 1-decene.…”

Section: Initial Doementioning

confidence: 99%

Design of Experiments for Process Optimization of the Direct Wacker-Type Oxidation of 1-Decene to n-Decanal

Bouveyron,

Bratenberg,

Bell

et al. 2024

Catalysts

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The rapid increase in the use and development of statistical design of experiments (DoE), particularly in pharmaceutical process development, has become increasingly important over the last decades. This rise aligns with Green Chemistry Principles, seeking reduced resource usage and heightened efficiency. In this study, we employed a comprehensive design of experiments (DoE) approach to optimize the catalytic conversion of 1-decene to n-decanal through direct Wacker-type oxidation using the previously determined efficient PdCl2(MeCN)2 catalytic system. The aim was to maximize selectivity and conversion efficiency. Through systematic variation of seven factors, including substrate amount, catalyst and co-catalyst amount, reaction temperature, reaction time, homogenization temperature, and water content, this study identified critical parameters influencing the process to direct the reaction toward the desired product. The statistical analysis revealed high significance for both selectivity and conversion, with surface diagrams illustrating optimal conditions. Notably, catalyst amount emerged as a pivotal factor influencing conversion, with reaction temperature and co-catalyst amount significantly affecting both conversion efficiency and selectivity. The refined model demonstrated strong correlations between predicted and observed values, highlighting the impact of these factors on both selectivity and conversion.

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Dichloro Bis(acetonitrile) Palladium

Cited by 9 publications

References 208 publications

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium‐Catalysed Cu‐Free Sonogashira Cross‐Coupling Reaction

Synthesis, Characterization, and Reaction Studies of Pd(II) Tripeptide Complexes

Design of Experiments for Process Optimization of the Direct Wacker-Type Oxidation of 1-Decene to n-Decanal

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