N-Heterocyclic Carbenes in Late Transition Metal Catalysis

Díez‐González, Silvia; Marion, Nicolas; Nolan, Steven P.

doi:10.1021/cr900074m

Cited by 2,859 publications

(1,173 citation statements)

References 1,033 publications

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“…These fluorescent NHC complexes, along with their precursor imidazolium salt (30) and (NHC)AuCl complex (31) and cisplatin, were tested against the human cancer cell lines A2780 (ovarian), MCF-7 (breast), and A549 (lung), with (non-cancerous) human embryonic kidney HEK-293T cells as a control. The precursors 30 and 31 showed much lower activity compared with cisplatin, while the glucosethiolate complex 32b showed only weak activity, and only against MCF-7 cells.…”

Section: Scheme 15mentioning

confidence: 99%

“…Carbohydrate N-heterocyclic carbene complexes in catalysis N-Heterocyclic carbenes have attracted interest as nucleophilic catalysts in, for example, polymerizations [29], but the main interest of NHCs in catalysis focuses on their use as ligands in catalytic metal complexes [30]. As ligands, NHCs have similar properties to phosphines, such as the ability to stabilise metals in various oxidation states [31], but NHC complexes have some significant advantages over phosphine complexes.…”

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confidence: 99%

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Carbohydrate– N -heterocyclic carbene metal complexes: Synthesis, catalysis and biological studies

Zhao

Ferro

Baker

2017

Coordination Chemistry Reviews

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Section: Scheme 15mentioning

confidence: 99%

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confidence: 99%

Carbohydrate– N -heterocyclic carbene metal complexes: Synthesis, catalysis and biological studies

Zhao

Ferro

Baker

2017

Coordination Chemistry Reviews

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“…25 The coordination of phosphines to the gold centre stabilise it and allows for improved reactivity. 26 NHC ligands provide an alternative steric profile, 27 and allow for different levels of σ-donation and π-backbonding, [28][29][30][31][32][33] which modifies the interactions of the gold complex with substrates that are bound trans-to the NHC. The highest catalytic turnover numbers (TONs) were obtained by Hashmi and coworkers.…”

Section: Introductionmentioning

confidence: 99%

The preference for dual-gold(i) catalysis in the hydro(alkoxylation vs. phenoxylation) of alkynes

et al. 2017

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This version is available at https://strathprints.strath.ac.uk/61289/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Herein we study the hydroalkoxylation and hydrophenoxylation of alkynes using density functional theory calculations, and compare two possible mechanisms that have been proposed previously on the basis of theoretical and experimental studies, which unravel different preferences because of both the nature of the alkyne and alcohol, as well as the non-innocent role of the counter-anion of the dual gold based catalyst. Entropy is found to have a significant effect, rendering the nucleophilic attack of the monoaurated intermediate [Au(L)(η 2 -alkyne)] + difficult both kinetically and thermodynamically; this mechanism cannot easily form only the trans-alkene product that is observed experimentally. Instead, reaction via a dual gold catalysed mechanism presents much lower barriers. In addition, for the sake of direct comparison with recent results by Belanzoni, Zuccaccia, oversimplification of the Nheterocyclic carbene (NHC) ligand in the calculations might decrease the enthalpy barrier and lead to results that are not directly applicable to experiment. Moreover, the alkylic or arylic nature of the alkyne and/or alcohol is also tested. ORGANIC & BIOMOLECULAR CHEMISTRY ARTICLE

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“…(Figure 2). [20][21][22] NHCs are mostly used as ligands for complexation reactions with transition metals like Ag(I), Pd(II), Pt(II), etc. The transition metal complexes of NHCs have been studied T and used as catalysts in various types of reactions such as polymerization, cyclization, reduction/oxidation, C-C bond formation/cleavage, hydrosilylation, etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Analysis and Antimicrobial Activities of Novel Water Soluble Ionic Liquids Derived from N-Heterocyclic Carbene Salts

Kunduracıoğlu¹,

Gübe²,

Hameş-Kocabaş³

et al. 2016

Croat. Chem. Acta

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Six N-heterocyclic Carbene based Ionic Liquids (ILs) have been synthesized by conventional methods. The ILs were spectroscopically characterized by NMR and FT-IR techniques. Their in vitro antimicrobial activities were determined towards gram-positive and gram-negative bacterias and yeast strains using minimum inhibition concentration (MIC) assay. The best inhibition performances were obtained with compound 1 due to its more hydrophilic nature compared with the others. It exhibited 1 mg L -1 MIC value against to the most bacteria while the others showed 4 mg L -1 .

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N-Heterocyclic Carbenes in Late Transition Metal Catalysis

Cited by 2,859 publications

References 1,033 publications

Carbohydrate– N -heterocyclic carbene metal complexes: Synthesis, catalysis and biological studies

Carbohydrate– N -heterocyclic carbene metal complexes: Synthesis, catalysis and biological studies

The preference for dual-gold(i) catalysis in the hydro(alkoxylation vs. phenoxylation) of alkynes

Synthesis, Structural Analysis and Antimicrobial Activities of Novel Water Soluble Ionic Liquids Derived from N-Heterocyclic Carbene Salts

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