Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

Dastgir, Sarim; Coleman, Karl S.; Green, Malcolm L. H.

doi:10.1039/c0dt00760a

Cited by 42 publications

(28 citation statements)

References 91 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first attempt to synthesize a Rh‐carbene complex from the imidazolium salt 1 followed the procedure reported by Dastgir and Green 24. This method was based on treatment of the imidazolium salt with Ag 2 O to afford the NHC‐Ag I complex followed by transmetallation with [Rh(μ‐Cl)(COD)] 2 .…”

Section: Resultsmentioning

confidence: 99%

Rhodium‐NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes

et al. 2014

View full text Add to dashboard Cite

Bis-silylated dihydroimidazolium salt 1 and monosilylated imidazolium salt 2 are transformed to (NHC)RhCl(COD) complexes 3 and 4, which allow the preparation of hybrid silica materials either by sol-gel or grafting processes. After a full characterization of the materials by means of solid state NMR, N2-sorption measurements, thermogravimetric analysis (TGA) and elemental analysis, the catalytic activity is evaluated in the [2+2+2] cycloaddition of alkynes. Excellent yields of the cycloadducts are obtained for up to six consecutive cycles with the grafted material, using a simple filtration to recover the catalyst. Both conventional and microwave heating prove to be effective for the process described.

show abstract

Section: Resultsmentioning

confidence: 99%

Rhodium‐NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes

et al. 2014

View full text Add to dashboard Cite

show abstract

“…To a 50‐mL Schlenk tube containing 10 mL of toluene, was added N ‐(2‐pyrimidyl)imidazole (62 mg, 0.42 mmol) and 3‐iodopropyl(trimethoxy)silane18 (121 mg, 0.42 mmol). The mixture was refluxed for 24 h, followed by the removal of the solvent using a rotary evaporator.…”

Section: Methodsmentioning

confidence: 99%

An Efficient and Recyclable Catalyst for N‐Alkylation of Amines and β‐Alkylation of Secondary Alcohols with Primary Alcohols: SBA‐15 Supported N‐Heterocyclic Carbene Iridium Complex

et al. 2013

View full text Add to dashboard Cite

A mesoporous silica (SBA-15)-supported pyrimidine-substituted N-heterocyclic carbene iridium complex was prepared and used as a catalyst for both environmentally friendly N-alkylation of amines and b-alkylation of secondary alcohols with primary alcohols. The structure of the supported iridium catalyst was characterized by Fourier transform infrared (FT-IR), 13 C and 29 Si solid-state nuclear magnetic resonance (NMR), small-angle X-ray scattering (SAXS), transmission electron microscopy (TEM), iridium K-edge X-ray absorption near-edge structure (XANES) and extended X-ray absorption fine structure (EXAFS) spectroscopic analyses which demonstrated that the coordination environment of the iridium centre and the 3-dimensional-hexagonal pore structure of SBA-15 were retained after the immobilization. The catalyst was found to be highly efficient for both kinds of reaction on a wide range of substrates under mild conditions. Moreover, the sup-ported iridium catalyst was obviously superior to the unsupported one in the N-alkylation of aniline and b-alkylation of 1-phenylethanol with benzyl alcohol as substrate, which indicated that not only the iridium complex moiety but also the support material contributed to the catalytic activity of the supported iridium catalyst in these reactions. The supported iridium catalyst can be easily recycled by simple washing without chemical treatment, and exhibited excellent recycling performance without notable decrease in catalytic efficiency even after twelve test cycles for N-alkylation of aniline with benzyl alcohol, nine cycles for N-alkylation of different amines with different alcohols, and eight cycles for b-alkylation of 1phenylethanol with benzyl alcohol, respectively.

show abstract

“…25 The improved synthesis route started from esters 14-16 that were obtained via esterification of pentafluorobenzoic acid. Next, the quaternarization reaction with 12 was conducted either directly (14) or after halogen atom exchange (17)(18) in acetone, 26 affording the formation of the QA moiety as linker unit. Finally, precursors 19-21 were treated with NaN 3 in acetone under reflux, 25 successfully producing target compounds 9-11.…”

Section: Precursor Synthesismentioning

confidence: 99%

Novel N-chloramine precursors for antimicrobial application: synthesis and facile covalent immobilization on polyurethane surface based on perfluorophenyl azide (PFPA) chemistry

Zhang

Gai

et al. 2018

Can. J. Chem.

View full text Add to dashboard Cite

To control the pathogen cross contaminations on medical material surface, there is a pressing need to develop antimicrobial materials with highly efficacious surface biocidal activity. In this work, N-chloramine precursors containing a quaternary ammonium unit and perfluorophenyl azide unit were synthesized and covalently immobilized on inert polyurethane (PU) film upon UV light irradiation. The surface modification was confirmed by contact angle, Fourier transform infrared (ATR FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS), and atomic force microscopy (AFM) analyses. After bleaching treatment, satisfactory biocidal activity was achieved for the surface-modified PU films. It was found that the introduced surface QA center contributed an even faster surface contact killing behavior and that precursors with a longer structural linker caused higher surface chlorine content and higher antimicrobial efficacy. This approach provides a novel and facile method that enables the covalent immobilization of N-chloramine precursors on inert polymeric surface to produce durable antimicrobial materials.

show abstract

Heterogenised N-heterocyclic carbene complexes: synthesis, characterisation and application for hydroformylation and C–C bond formation reactions

Cited by 42 publications

References 91 publications

Rhodium‐NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes

Rhodium‐NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes

An Efficient and Recyclable Catalyst for N‐Alkylation of Amines and β‐Alkylation of Secondary Alcohols with Primary Alcohols: SBA‐15 Supported N‐Heterocyclic Carbene Iridium Complex

Novel N-chloramine precursors for antimicrobial application: synthesis and facile covalent immobilization on polyurethane surface based on perfluorophenyl azide (PFPA) chemistry

Contact Info

Product

Resources

About