Polymer-supported N-heterocyclic carbene–rhodium complex catalyst for the addition of arylboronic acids to aldehydes

Yan, Chun; Zeng, Xiaoming; Zhang, Weifeng; Luo, Meiming

doi:10.1016/j.jorganchem.2006.02.021

Cited by 25 publications

(7 citation statements)

References 47 publications

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“…To prepare the PS-supported NHC–Rh complexes 670 and 671 , KO t Bu and [RhCl(COD)] 2 were reacted with the corresponding NHC precursor in THF solution (Scheme ). , On the other hand [Ir(COD)(μ-OMe)] 2 could be used as an internal base to directly deprotonate the carbon-supported NHC precursors 264 – 267 , 195 , and 209 in THF (Scheme ), preparing the supported NHC–Ir compounds 672 – 678 . ,,, Similarly, [Rh(COD)(μ-OMe)] 2 has been used to synthesize PS-supported Rh–NHC complexes 675 and 676 starting from precursors 195 and 209 . Alternatively, the silver transmetalation approach was applied for the synthesis of silica supported NHC–Ir complex 679 ( 680 ) from [Cp*IrCl 2 ] 2 and 653 ( 654 )-type Ag–NHC (short rigid linker to the NHC moiety). ,, Using a more flexible linker to the NHC moiety and [IrCl(COD)] 2 , the oxygen-stabilized silica supported NHC–Ir compound 681 was obtained (Scheme ).…”

Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

et al. 2017

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Over the course of the past 15 years the success story of N-heterocyclic carbene (NHC) compounds in organic, inorganic, and organometallic chemistry has been extended to another dimension. The immobilization of NHC compounds, undergoing continuous diversification, broadens their range of applications and leads to new solutions for challenges in catalytic and synthetic chemistry. This review intends to present a synthetic toolkit for the immobilization of NHC compounds, giving the reader an overview on synthetic techniques and strategies available in the literature. By individually summarizing and assessing the synthetic steps of the immobilization process, a comprehensive picture of the strategies and methodologies for the immobilization of NHC compounds is presented. Furthermore, the characterization of supported NHC compounds is discussed in detail in order to set up necessary criteria for an in-depth analysis of the immobilized derivatives. Finally, the catalytic applications of immobilized NHC compounds are briefly reviewed to illustrate the practical use of this technique for a broad variety of reaction types.

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Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

et al. 2017

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“…35c The Luo group prepared chloromethyl polystyrene supported NHC-Rh P5 with a rhodium loading of 0.18 mmol g À1 . 36 The catalytic activity of the heterogeneous system was studied in the addition of phenylboronic acid to p-substituted benzaldehydes Scheme 1 Wang resin-supported NHC-Pd complex P1 for a Heck coupling reaction by Herrmann et al 33 Scheme 2 Polystyrene-supported NHC-Pd complexes P2 and P3 for the Suzuki cross coupling by Lee et al 34 at 80 1C. Various aryl aldehydes underwent addition reactions with various phenylboronic acids to afford arylmethanols in good to excellent yields (up to 95%) in 1,4-dioxane-water (4 : 1) (Scheme 4).…”

Section: Nhcs Supported On Organic Polymersmentioning

confidence: 99%

“…Furthermore, Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES) analysis after the reaction indicated Pd was not leached from the support during the catalysis. Scheme 4 Addition of phenylbororonic acid to aldehydes catalyzed by the polystyrene resin-supported NHC-Rh complex P5 by Luo et al 36 Scheme 5 Suzuki and Heck coupling reactions catalyzed by the polymersupported NHC-Pd complex P6 derived from nicotinic acid. 37a One of the advantages of soluble polymer catalysts is their isolability, even though the activity is similar to a homogeneous system.…”

Section: Nhcs Supported On Organic Polymersmentioning

confidence: 99%

Recent progress of N-heterocyclic carbenes in heterogeneous catalysis

Ranganath

Onitsuka

Kumar

et al. 2013

Catal. Sci. Technol.

118

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The aim of this tutorial review is to highlight the potential application of N-heterocyclic carbenes (NHC) in heterogeneous catalysis. The unique combination of the high reactivity of NHCs together with the ease of separation, purification and recyclability of the solid catalyst makes the heterogeneous system one of the most promising strategies for the synthesis of fine chemicals on an industrial scale. This tutorial review focuses on the most representative examples of this nascent research area and highlights recent achievements of NHCs in heterogeneous catalysis (other than metathesis reactions).We hope this serves as inspiration for further progress in this field.

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“…Luo and co-workers also developed a polystyrene-supported NHC-Rh complex catalyst ( 271 ) through a solid phase synthesis strategy that started from chloromethyl polystyrene (CM PS) resin (Scheme ). This polymer-supported NHC-Rh complex was applied as a heterogeneous catalyst for the addition of arylboronic acids to aldehydes affording arylmethanols in satisfactory yields. The heterogeneous catalyst 271 could be easily recovered through a filtration process, and after six runs’ reuse under the same reaction conditions, the catalyst retained good activity.…”

Section: Immobilized (Heterogenized) Nhc Complex Catalystmentioning

confidence: 99%

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

et al. 2018

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With the continuous development of N-heterocyclic carbene (NHC) chemistry during the past decade, NHC metal complexes have gained wide applications in the research field of organometallic catalysis. The recycling and reuse of NHC metal complexes, which have undergone continuous expansion and diversification, can enhance their catalytic performance, extend their range of application, and afford new routes to green chemistry. Taking NHC metal complex catalysts as the main topic, this review intends to present a comprehensive study of recycling strategies of organometallic catalysts. By an elaborative summarization and classification of recycling strategies, a clear picture of all available of recycling strategies for organometallic catalysts is presented and the advantages and disadvantages of various recycling strategies for specific reactions are discussed in detail. This review is written with the hope of serving as a modest spur to induce other scientists' further contributions in the fields of catalyst recycling and sustainable catalysis.

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Polymer-supported N-heterocyclic carbene–rhodium complex catalyst for the addition of arylboronic acids to aldehydes

Cited by 25 publications

References 47 publications

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

Recent progress of N-heterocyclic carbenes in heterogeneous catalysis

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

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