A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water

Balaswamy, K.; Perumgani, C Pullaiah; Mandapati, Mohan Rao

doi:10.1016/j.apcata.2014.07.001

Cited by 28 publications

(13 citation statements)

References 34 publications

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“…Currently, the heterogeneous catalytic systems seem to arouse the particular interest of researchers due to the simplicity of their isolation and re‐use. Several examples of the heterogeneous copper catalysts active in the C‐N and A 3 coupling reactions were described previously. Different inorganic materials (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Bukowska

Bukowski

Bester

et al. 2017

Applied Organom Chemis

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New polymer supported Cu(II) complexes based on an epoxy functionalized gel type resin were prepared using the multi-stage procedures. The reactions of epoxy groups with ethylenediamine or tris(2-aminoethyl)amine, and then NH 2 groups with salicylaldehydes were used for the preparation of a series of amine-imine functionalized polymer supports. Copper(II) acetate was used as a source of metal ions. The complexes were characterized using ICP-OES, FTIR, DR UV-Vis and TGA techniques, and tested as catalysts in two model C-N and a series of A 3 coupling reactions. Their catalytic activity was rather low in the C-N coupling reactions between imidazole and iodobenzene or phenylboronic acid. However, the second of the reactions could be conducted effectively under milder conditions. The complexes were efficient used as recyclable catalysts in the A 3 coupling reactions.A series of aromatic aldehydes and secondary amines and phenylacetylene could be coupled using 1% mol catalyst.

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Section: Introductionmentioning

confidence: 99%

“…Different inorganic materials (e.g. fluoroapatite, silica,), organic polymers, including biopolymers (e.g. cellulose, chitosan) were tested as supports for the copper catalysts.…”

Section: Introductionmentioning

confidence: 99%

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Bukowska

Bukowski

Bester

et al. 2017

Applied Organom Chemis

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“…After four recycles loss of 7% was observed. This catalyst was also applied in N-arylation of indoles [79]. In 2011, a new concept of heterogeneous materials based on highly cross-linked imidazolium salts anchored on silica gel as supports for palladium nanoparticles in high loadings was developed [80].…”

Section: C-c Coupling Reactionsmentioning

confidence: 99%

“…Kodicherla et al reported the first Sonogashira coupling reaction catalysed by polystyrenesupported Cu(II) complex [79]. The polystyrene-supported Cu(II) N,N-dimethyl-ethylenediamine complex 136 was prepared by treatment of polymer-bound N,N-dimethylethylenediamine 135 with an ethanolic solution of CuBr 2 at 50 • C (Scheme 49).…”

Section: C-c Coupling Reactionsmentioning

confidence: 99%

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Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

2016

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Abstract:In this review, the most recent advances (2014)(2015)(2016) on the synthesis of new polymer-supported catalysts are reported, focusing the attention on the synthetic strategies developed for their preparation. The polymer-supported catalysts examined will be organic-based polymers and organic-inorganic hybrids and will include, among others, polystyrenes, poly-ionic liquids, chiral ionic polymers, dendrimers, carbon nanotubes, as well as silica and halloysite-based catalysts. Selected examples will show the synthesis and application in the field of organocatalysis and metal-based catalysis both for non-asymmetric and asymmetric transformations.

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An efficient, mild and selective Ullmann‐type N‐arylation of indoles catalysed by Pd immobilized on amidoxime‐functionalized mesoporous SBA‐15 as heterogeneous and recyclable nanocatalyst

Ghorbani‐Vaghei

Hemmati

Hamelian

et al. 2015

Applied Organom Chemis

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A wide range of N-arylated indoles were selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of Pd immobilized on amidoxime-functionalized mesoporous SBA-15 (SBA-15/AO/Pd(0)) under mild reaction conditions. These crosscoupled products were obtained in excellent yields under mild conditions at extremely low palladium loading (ca 0.3 mol%), and the heterogeneous catalyst can be readily recovered by simple filtration and reused seven times with loss in its activity.

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A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water

Cited by 28 publications

References 34 publications

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

An efficient, mild and selective Ullmann‐type N‐arylation of indoles catalysed by Pd immobilized on amidoxime‐functionalized mesoporous SBA‐15 as heterogeneous and recyclable nanocatalyst

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A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water

Cited by 28 publications

References 34 publications

Polymer supported copper(II) amine‐imine complexes in the C‐N and A3 coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A3 coupling reactions

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

An efficient, mild and selective Ullmann‐type N‐arylation of indoles catalysed by Pd immobilized on amidoxime‐functionalized mesoporous SBA‐15 as heterogeneous and recyclable nanocatalyst

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Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions

Polymer supported copper(II) amine‐imine complexes in the C‐N and A³ coupling reactions