Polystyrene supported salen type bis-thiopseudourea Pd(II)-complex catalyzed Suzuki coupling reaction in aqueous media

Srinivas, K.; Mandapati, Mohan Rao; Parvathaneni, Sai Prathima

doi:10.1016/j.apcata.2015.02.029

Cited by 31 publications

(3 citation statements)

References 36 publications

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“…However, they cannot be reused, resulting in a loss of expensive Pd metal and organic ligands . In the last decades, great attention was given to so-called ligandless palladium catalysts based on zeolites, , metal–organic frameworks, , metal oxides, − resins, , activated carbon, ,, carbon nanotubes, and graphenes . Their main advantage is easy separation from the reaction mixture and possibility of reuse .…”

Section: Introductionmentioning

confidence: 99%

Au Core–Pd Shell Bimetallic Nanoparticles Immobilized within Hyper-Cross-Linked Polystyrene for Mechanistic Study of Suzuki Cross-Coupling: Homogeneous or Heterogeneous Catalysis?

Nemygina

Nikoshvili

Tiamina

et al. 2018

Org. Process Res. Dev.

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The synthesis of catalytically active bimetallic Au–Pd nanoparticles stabilized in hyper-cross-linked polystyrene (HPS) for Suzuki cross-coupling of 4-bromoanisole (4-BrAn) and phenylboronic acid is presented. The core–shell structure with a thin (less than 1 nm) Pd shell and a Au core was proven by X-ray diffraction and high-angle annular dark-field scanning transmission electron microscopy combined with energy-dispersive X-ray spectroscopy. More than a 2-fold increase in 4-BrAn conversion was found in comparison with monometallic Pd/HPS. Moreover, when the Suzuki reaction was carried out under visible-light irradiation, the product yield further increased by about 1.3 times (from 56.1% up to 73.7%). This effect was assigned to a local surface plasmon resonance arising in the Au core that allowed electron transfer to the extremely thin Pd layer due to intimate contact with gold. The results suggest that the rate-limiting step of the catalytic cycle takes place on the surface of the Pd shell, serving as evidence of the heterogeneous catalysis nature.

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Section: Introductionmentioning

confidence: 99%

Au Core–Pd Shell Bimetallic Nanoparticles Immobilized within Hyper-Cross-Linked Polystyrene for Mechanistic Study of Suzuki Cross-Coupling: Homogeneous or Heterogeneous Catalysis?

Nemygina

Nikoshvili

Tiamina

et al. 2018

Org. Process Res. Dev.

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“…Palladium-catalyzed Suzuki cross-coupling between aryl halides and arylboronic acids is one of the most widespread and effective methods of synthesis of biaryls, which are in turn important semiproducts in the synthesis of pharmaceuticals, ligands, and polymers. − There are more than three hundred various commercial compounds which can react via Suzuki coupling and a huge diversity of Pd-containing catalysts . The latter include the following: homogeneous Pd complexes; − so-called ligandless catalysts containing Pd 2+ or Pd 0 , which are Pd salts, , Pd deposited on inorganic supports, − Pd deposited on carbon − or nonfunctionalized polymers, − or Pd nanoparticles (NPs) stabilized in magnetically separable nanocomposites; , Pd immobilized via ionic or covalent interactions on ligand-containing polymers (including functionalized dendrimers, carbon nanotubes, graphenes, resins, − and other polymers − ) or on magnetic NPs with anchored ligands. ,− …”

Section: Introductionmentioning

confidence: 99%

“…Pd immobilized via ionic or covalent interactions on ligand-containing polymers (including functionalized dendrimers, carbon nanotubes, graphenes, resins, − and other polymers − ) or on magnetic NPs with anchored ligands. ,− …”

Section: Introductionmentioning

confidence: 99%

Catalysts of Suzuki Cross-Coupling Based on Functionalized Hyper-cross-linked Polystyrene: Influence of Precursor Nature

Nemygina

Nikoshvili

Быков

et al. 2016

Org. Process Res. Dev.

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This paper describes synthesis of Pd-containing catalysts of Suzuki cross-coupling based on amino-functionalized hyper-cross-linked polystyrene at variation of Pd precursor nature (PdCl 2 , PdCl 2 (CH 3 CN) 2 , or PdCl 2 (PhCN) 2 ). The investigation of the influence of palladium oxidation state (Pd(II) or Pd(0)) and form (Pd n clusters or Pd nanoparticles) on the rate of Suzuki cross-coupling of 4-bromoanisole and phenylboronic acid is discussed. Developed catalysts are shown to allow achieving conversion of 4-bromoanisole higher than 98% under mild reaction conditions. Independently of the precursor nature, Pd(II) is mainly responsible for observed catalytic activity. However, preliminary reduction of catalysts with H 2 results in formation of a large number of Pd n clusters, the contribution of which in the Suzuki reaction becomes predominant.

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Polystyrene‐supported Pd(II) complex‐catalysed carboacylation of 2‐arylpyridines with alcohols via C─H bond activation under solvent‐free conditions

Perumgani

Parvathaneni

Keesara

et al. 2016

Applied Organom Chemis

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Polystyrene‐supported N,N‐dimethylethylenediamine Pd(II) complex C was used as an efficient catalyst for the synthesis of aromatic ketones via ortho‐acylation of sp2 C─H bonds of 2‐arylpyridines with alcohols as effective coupling partners. The alcohols were oxidized with tert‐butyl hydroperoxide to their corresponding aldehydes in situ and efficiently coupled with 2‐arylpyridines to form aryl ketones under solvent‐free conditions. Furthermore, catalyst C could be easily recovered by simple filtration and reused for five cycles without any significant decrease in its activity.

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Polystyrene supported salen type bis-thiopseudourea Pd(II)-complex catalyzed Suzuki coupling reaction in aqueous media

Cited by 31 publications

References 36 publications

Au Core–Pd Shell Bimetallic Nanoparticles Immobilized within Hyper-Cross-Linked Polystyrene for Mechanistic Study of Suzuki Cross-Coupling: Homogeneous or Heterogeneous Catalysis?

Au Core–Pd Shell Bimetallic Nanoparticles Immobilized within Hyper-Cross-Linked Polystyrene for Mechanistic Study of Suzuki Cross-Coupling: Homogeneous or Heterogeneous Catalysis?

Catalysts of Suzuki Cross-Coupling Based on Functionalized Hyper-cross-linked Polystyrene: Influence of Precursor Nature

Polystyrene‐supported Pd(II) complex‐catalysed carboacylation of 2‐arylpyridines with alcohols via C─H bond activation under solvent‐free conditions

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