Preparation, characterization and first application of silica supported palladium-N-heterocyclic carbene as a heterogeneous catalyst for C–C coupling reactions

Ghiaci, Mehran; Zarghani, Monireh; Khojastehnezhad, Amir; Moeinpour, Farid

doi:10.1039/c4ra00002a

Cited by 39 publications

(25 citation statements)

References 35 publications

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“…27 In another aspect, various nanoparticles or micro-particles have been reported and widely used as the carrier of solid catalysts. 10,11,16,19,20,28,29 Among those materials, the mesoporous silica nanoparticles is highly attractive by virtue of its large specic surface area, facile modication for diverse functions and heat-and hydro-stability. [30][31][32] Amini et al reported a heterogeneous palladium catalyst by anchoring tridentate pyridine ligand to mesoporous silica, which showed good capacity in catalyzing Mizoroki-Heck and Suzuki-Miyaura reaction with 1 mol%.It could be recycled for four times but loss of catalytic activity aer each recycle was noted.…”

Section: Introductionmentioning

confidence: 99%

“…17,18 Various ligands that have been immobilized for chelating of palladium ions include thiol groups, heterocyclic ring structure, multi-oxygen or nitrogen groups and other groups. 11,[19][20][21][22][23] In recent years, the uorescent probes for the detection and separation of heavy metal ions, such as palladium ions, has gained extensive interest. These studies have inspired constructing multifunctional platforms for ion detection, separation and reusability onto host materials.…”

Section: Introductionmentioning

confidence: 99%

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A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki–Miyaura reaction in pure water under air

Cai

Liang

et al. 2016

RSC Adv.

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Herein, we report a heterogenous catalyst (Pd@FSM) by immobilization of a novel Pd 2+ sensor as promoter over mesoporous silica. Pd@FSM with a high palladium loading of ca. 11 mg g À1 exhibited superior catalytic activity for Suzuki-Miyaura cross-couplings and a catalyst loading of 0.05 mol% is typically sufficient to achieve excellent reaction yields. Notably, the reaction is typically carried out in water without removing atmospheric oxygen. The catalyst is conveniently recycled and remains highly active even after being recycled 5 times. During this process, loss of palladium from the solid support of the catalyst is negligible. Furthermore, the catalyst can be stored in air for at least three months without loss of its catalytic activity. This work provides a new approach to developing heterogeneous palladium catalysts by combing materials and fluorescent sensors.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki–Miyaura reaction in pure water under air

Cai

Liang

et al. 2016

RSC Adv.

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“…In this case, aryl chlorides were not suitable, but good yields were obtained in the reaction between aromatic iodide and bromide derivatives and phenylacetylene. The recovery and reusability of the catalyst was demonstrated by using it in five runs without detrimental in the obtained results [76]. and bromide derivatives and phenylacetylene.…”

Section: Functionalized Silica-supported Palladium Catalystsmentioning

confidence: 99%

“…and bromide derivatives and phenylacetylene. The recovery and reusability of the catalyst was demonstrated by using it in five runs without detrimental in the obtained results [76]. The silica surface can be modified by grafting polymeric chains, combining the compatibility of the interfacial polymer with the organic solvents and the high mechanical stability of the silica ( Figure 14).…”

Section: Functionalized Silica-supported Palladium Catalystsmentioning

confidence: 99%

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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Abstract:The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions.

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“…122 Recovery was accomplished in five sequential reaction runs (Table 13, entries 1-7). quantitative yield of the desired coupling product (95%), the catalyst was recovered and successively subjected to the next run under the same conditions to afford the product in good to excellent yields for up to five cycles (Table 13, entries 8-19).…”

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confidence: 99%

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Gürbüz¹,

Karaca²,

Özdemır³

et al. 2015

Turk J Chem

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This review is focused on new developments reported during the last 3 years concerning the catalytic performances of in situ formed or preformed NHC-Pd(II) complexes (NHC: N -heterocyclic carbene) for cross-coupling reactions such as Heck-Mizoraki (often shortened to the Heck reaction), Kumada, Negishi, Suzuki-Miyaura (often shortened to the Suzuki reaction), Sonogashira and Hiyama couplings, and the Buchwald-Hartwig aminations, which are extremely powerful in the formation of C-C and C-heteroatom bonds. Due to the great number of publications and limited space here, we made a special attempt to compile the relevant data in tables, which we hope will serve as a guide for chemists interested in these reactions. The syntheses of the precatalysts and the generally accepted reaction mechanisms are also briefly described.

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Preparation, characterization and first application of silica supported palladium-N-heterocyclic carbene as a heterogeneous catalyst for C–C coupling reactions

Cited by 39 publications

References 35 publications

A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki–Miyaura reaction in pure water under air

A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki–Miyaura reaction in pure water under air

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

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