Catalytic activity of some palladium complexes of a phosphorus ylide and the structure of a 2-phenylaniline-based palladacycle complex

Karami, Kazem; Rahimi, Nasser Mohammad; Rizzoli, Corrado

doi:10.1016/j.poly.2013.04.055

Cited by 9 publications

(2 citation statements)

References 41 publications

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“… [21] With 2.0 mol % of 9 , the reaction worked well at 60 °C to give the coupled products in good to excellent yields. Two years later, they reported the synthesis of three new P ‐ylide‐Pd complexes, and found that the use of 2.0 mol % 10 provided a comparable result in the same Suzuki‐Miyaura reactions [22] . By contrast, the catalytic activity of these P ‐ylide‐Pd complexes is higher than that of N,C ‐palladacycle 11 with a 2‐phenylaniline bidentate ligand.…”

Section: P‐ylide‐metal Complex Catalysismentioning

confidence: 99%

Recent Advances in Applying Carbonyl‐stabilized Phosphorus Ylides for Catalysis

Shi

Pan

et al. 2020

ChemCatChem

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The exploration of new catalytic properties of the known functionalities would facilitate the exploitation of new ligands and/or organocatalysts that are able to achieve reactivity and selectivity unattainable by known ones. In this context, carbonyl‐stabilized phosphorus ylides have emerged as a type of novel ligand motifs and organocatalysts, exhibiting versatile catalytic activity towards some important organic reactions such as cross‐couplings, cyanation, CO2 fixation. This Minireview summarizes these recent advances, highlights the advantages and limitations, and outlines synthetic opportunities still open for further investigation.

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Section: P‐ylide‐metal Complex Catalysismentioning

confidence: 99%

Recent Advances in Applying Carbonyl‐stabilized Phosphorus Ylides for Catalysis

Shi

Pan

et al. 2020

ChemCatChem

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“… − The strong σ-donating and weak π-accepting abilities of NHC ligands often impart enhanced catalytic activity and improved stability in many transition metal complexes, particularly Pd and Ni complexes that are widely used in catalytic organic cross-coupling reactions. − Like NHCs, organic ylides, most notably phosphorus ylides (P-ylides), comprise an alternative family of Lewis basic carbon donor (C-donor) ligands capable of coordinating a wide range of main group and transition metal centers ( 2 , Scheme ). − Moreover, experimental evidence indicating that phosphorus ylides are stronger C-donor ligands than many NHCs has been reported. , Notably, however, utilization of P-ylide metal complexes in homogeneous catalysis has received scant attention. − In addition, other types of C-donor ligands for catalytically relevant transition metals have not been extensively developed.…”

Section: Introductionmentioning

confidence: 99%

Groups 9 and 10 Complexes of C–Donor Ligands Derived from Pyridinium-Stabilized Phosphorus Ylides

Poddar,

Pigge

2024

Organometallics

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The design and synthesis of η 1 -C-donor ligands that combine nucleophilic 4-alkylidene dihydropyridines with phosphorus ylides is reported. Positioning of a phosphonium group at the picolyl carbon of 4-alkylpyridinium salts allows for conversion to phosphonium-stabilized alkylidene dihydropyridine ligands under mildly basic conditions. The resulting (Me-N-Py-CH-PPh 2 -R)(BF 4 ) ligands coordinate Pd(II)Cl 2 as monodentate (R = Ph) or bidentate ligands (R = 2-Py, CH 2 PPh 2 , or CH 2 CH 2 PPh 2 ), and six new Pd(II) complexes were spectroscopically characterized. Structural features of four of the complexes were further defined through single-crystal X-ray diffractometry. The ligands in these complexes are best described as phosphorus ylide C-donors that are stabilized by adjacent N-methylpyridinium rings. In addition, two Rh(I) complexes were successfully prepared and characterized, including a Rh(I) carbonyl complex which exhibited a low ν CO of 1984 cm −1 , indicative of the strong σ-donor properties of these ligands. The ability of a Pd complex to catalyze Suzuki cross-coupling reactions was examined.

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