Palladium complexes containing NNN pincer type ligands and their activities in Suzuki-Miyaura cross coupling reaction

Keskin, Ebru; Arslan, Hakan

doi:10.1016/j.heliyon.2023.e17608

Cited by 9 publications

(2 citation statements)

References 76 publications

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“…Overall, the catalytic activity presented by Ni or Co pincer complexes in Suzuki-Miyaura reactions demonstrates their viability on the production of small biaryl molecules reaching reaction yields around 90% using up to 5.0 mol% catalyst loading. Despite having results slightly close to those obtained with Pd(II) analogs (>94 mol%) [75,76], the reduction in the catalyst loading remains the main challenge for researchers. Therefore, efforts have been focused on understanding the reaction conditions and the electronic properties of ligands and their effect on the catalytic properties of the resulting pincer complexes with the purpose of reducing the catalyst loading in an efficient way.…”

Section: Suzuki-miyaura Cross-couplingmentioning

confidence: 98%

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Cruz-Navarro,

Sánchez-Mora,

Serrano-García

et al. 2024

Catalysts

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The increase of noble-metal-free catalysis in organic chemistry is a trending topic in constant growth due to the price increase of noble metals and their scarce abundance. As a result, many earth-abundant transition-metal complexes containing nickel, iron, or cobalt have been successfully applied in the homogeneous catalysis of a wide number of cross-coupling reactions, and the use of pincer complexes based on these earth-abundant metals was recently explored, affording interesting results. Thus, this review provides a general overview of earth-abundant 3D pincer complexes and their application during the last decade as catalysts in cross-coupling reactions such as Kumada–Corriu, Suzuki–Miyaura, Sonogashira, C–S cross-coupling, and C–N bond-forming reactions.

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Section: Suzuki-miyaura Cross-couplingmentioning

confidence: 98%

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Cruz-Navarro,

Sánchez-Mora,

Serrano-García

et al. 2024

Catalysts

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“…In situ -generated palladium nanoparticles stabilized by phosphine ligands have shown excellent catalytic activity in organic synthesis . The less expensive in situ -generated Pd NPs under milder and less hazardous conditions have shown enhanced catalytic activity compared to that of molecular complexes …”

Section: Introductionmentioning

confidence: 99%

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

Sheokand

Balakrishna

2023

Inorg. Chem.

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We describe the synthesis of a triazolyl-pyridine-based aminophosphine, N-(diphenylphosphaneyl)-6-(1-phenyl)-1H- (1,2,3-triazol-4-yl)H)N hereafter], and its palladium and platinum complexes and their catalytic application. The reaction of 1 with [M(COD)Cl 2 ] (M = Pd or Pt) afforded the cationic complex [(MCl){PN(H)N}-κ 3 -P,N,N]Cl [M = Pd (2) or Pt (3)]. Alternatively, compounds 2 and 3 were also synthesized by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M(COD)Cl 2 ] (M = Pd or Pt), followed by the addition of stoichiometric amounts of PPh 2 Cl and Et 3 N. The neutral, dearomatized complexes [(MCl){PNN}-κ 3 -P,N,N] [M = Pd (4) or Pt (5)] were prepared by the deprotonation of the NH of 2 and 3 with 1 equiv of t BuOK. Compounds 4 and 5 were also synthesized stepwise by treating [2,6-{H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] (A) with [M-(COD)Cl 2 ] (M = Pd or Pt) to give intermediate complexes [{MCl 2 }2,6-{NH 2 (C 5 H 3 N)(C 2 HN 3 C 6 H 5 )-κ 2 -N,N}] [M = Pd (B) or Pt (C)], which were subsequently phosphinated. The in situ-generated PNN ligand-stabilized Pd nanoparticles from compound 2 catalyzed the annulation of o-bromobenzaldehyde with alkynes to yield indenone derivatives. Mechanistic investigations suggested that the reaction was catalyzed by Pd nanoparticles (Pd@2) generated from compound 2 and proceeded through sequential oxidative addition, alkyne insertion, and reductive elimination steps to produce indanone products.

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NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction

Xu,

Wang,

et al. 2024

Transit Met Chem

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A series of novel NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands 6 were prepared and characterized by spectroscopic methods. In addition, the molecular structures of complexes 6a and 6i have also been determined by X-ray single-crystal diffraction.The obtained palladium(II) catalysts showed efficient catalytic activity toward the Heck coupling of aryl bromides with olefins. Under the optimal reaction conditions, the expected various styrenes were obtained in moderate to high yields.

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Palladium complexes containing NNN pincer type ligands and their activities in Suzuki-Miyaura cross coupling reaction

Cited by 9 publications

References 76 publications

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction

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Palladium complexes containing NNN pincer type ligands and their activities in Suzuki-Miyaura cross coupling reaction

Cited by 9 publications

References 76 publications

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

Cationic and Neutral PdII and PtII Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones

NNN pincer palladium(II) complexes with N-(2-(1H-pyrazol-1-yl)phenyl)-picolinamide ligands: synthesis, characterization, and application to heck coupling reaction

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Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones