Polymer-Supported <i>N</i>-Heterocyclic Carbene−Palladium Complex for Heterogeneous Suzuki Cross-Coupling Reaction

Kim, Jong-Ho; Kim, Jung-Woo; Shokouhimehr, Mohammadreza; Lee, Jun Young

doi:10.1021/jo050721m

Cited by 232 publications

(112 citation statements)

References 49 publications

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“…16 However, also the incorporation of NHCs into a polymer backbone has been reported to increase their stability. 17 Recent studies showed that functionalized NHCs can also be applied as maintaining part of metal organic frameworks (MOFs) 18 or in polymer networks with intrinsic microporosity (PIMs). 19,20 The latter materials are prepared from rigid and contorted molecules, oen called knots or tectons which are polymerized either directly or using linear linkers.…”

Section: N-heterocyclic Carbenes (Nhcs)mentioning

confidence: 99%

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks

et al. 2013

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A polymer analogous reaction was carried out to generate a porous polymeric network with N-heterocyclic carbenes (NHC) in the polymer backbone. Using a stepwise approach, first a polyimine network is formed by polymerization of the tetrafunctional amine tetrakis(4-aminophenyl)methane. This polyimine network is converted in the second step into polyimidazolium chloride and finally to a polyNHC network.Furthermore a porous Cu(II)-coordinated polyNHC network can be generated. Supercritical drying generates polymer networks with high permanent surface areas and porosities which can be applied for different catalytic reactions. The catalytic properties were demonstrated for example in the activation of CO 2 or in the deoxygenation of sulfoxides to the corresponding sulfides.

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Section: N-heterocyclic Carbenes (Nhcs)mentioning

confidence: 99%

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks

et al. 2013

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“…In particular the use of a soluble polymer support to immobilize N-heterocyclic carbene metal complexes has often been limited to one catalytic moiety per polymer chain. [50,[54][55][56][57] One exception to this is the work by Buchmeiser et al, whose group reported the functionalization of insoluble monolithic polymer discs with a variety of ruthenium catalysts using elegant post-polymerization functionalizations. [58] In this contribution, we report the synthesis of supported NHCs using poly(norbornene) as soluble polymer support.…”

Section: Introductionmentioning

confidence: 99%

Poly(norbornene)‐Supported N‐Heterocyclic Carbenes as Ligands in Catalysis

Sommer

Weck

2006

Adv Synth Catal

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In this contribution, we present the synthesis of norbornene-supported N-heterocyclic (NHC) carbenes. These functionalized norbornenes were polymerized via ring-opening metathesis polymerization in a controlled fashion either before or after metalation with a variety of palladium and ruthenium precursors resulting in the formation of polymersupported NHC-based metal catalysts. The activities of the palladium-based catalysts in the SuzukiMiyaura, Sonogashira and Heck coupling reactions were studied in detail. In all cases, the polymeric catalysts demonstrated the same activity as their small molecule analogues. Furthermore, we carried out preliminary investigations into the stability of these catalysts using poisoning studies. A clear dependence of the stability of the polymer-supported catalysts on their palladium precursor was observed with palladium acetate-based polymeric NHC catalysts being the most stable. Finally, we have studied the reactivity of our supported NHC ruthenium complexes as catalysts for ring-closing metathesis. Again, in all cases good conversions were observed with comparable activities to other supported NHC-ruthenium catalysts. Lastly, we were able to remove the ruthenium catalysts from the solution quantitatively demonstrating the possibility of metal removal.

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“…[13][14][15][16] The catalyst NPs grafted or immobilized on the surface of the supports also provide accessible diffusion to reagents, and result in more effective chemical reactions. 17,18 Among the various nanostructured materials, magnetic NPs have attracted growing interest owing to their unique properties and potential applications in various fields, including isolation and recycling of expensive catalysts NPs. [19][20][21] Magnetic separation provides a convenient method for removing and recycling magnetized species by applying an appropriate magnetic field.…”

Section: -3mentioning

confidence: 99%

Heterogeneous Suzuki Cross-Coupling Reaction Catalyzed by Magnetically Recyclable Nanocatalyst

Choi¹,

Shokouhimehr²,

Sung³

2013

Bulletin of the Korean Chemical Society

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The Suzuki cross-coupling reactions proceeded in excellent yields when it was catalyzed by magnetically recyclable nanocatalyst. This nanocatalyst provided very high catalytic activity with low loading level (1 mol %), because the palladium nanoparticles were so small in size (~2 nm) and located on the surface of the nanocomposite. It was also easily recovered from the reaction mixture using a magnet and reused for six consecutive cycles.

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Polymer-Supported N-Heterocyclic Carbene−Palladium Complex for Heterogeneous Suzuki Cross-Coupling Reaction

Cited by 232 publications

References 49 publications

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks

A polymer analogous reaction for the formation of imidazolium and NHC based porous polymer networks

Poly(norbornene)‐Supported N‐Heterocyclic Carbenes as Ligands in Catalysis

Heterogeneous Suzuki Cross-Coupling Reaction Catalyzed by Magnetically Recyclable Nanocatalyst

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