Recent advances in the chemistry and applications of N-heterocyclic carbenes

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(10), P. 711 - 725

Published: Sept. 3, 2021

Language: Английский

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N‐Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 38(10), P. 1167 - 1202

Published: May 10, 2020

N ‐Heterocyclic carbene (NHC) organocatalysis has been developed as an important approach in modern organic synthesis. Versatile activation modes within NHC have established with countless transformations being realized both efficient and selective fashion. We would like to provide overview on the key progresses achieved this field past two decades. Since numerous excellent reviews documented area, we will mainly focus scientific development of research based basic reaction typical intermediates.

Language: Английский

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Synthetic Routes to Late Transition Metal–NHC Complexes

Trends in Chemistry, Journal Year: 2020, Volume and Issue: 2(8), P. 721 - 736

Published: June 30, 2020

Language: Английский

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Advances in chemistry of N-heterocyclic carbene boryl radicals

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(16), P. 8995 - 9021

Published: Jan. 1, 2021

This review focuses on synthesis and reactions of boryl radicals ligated by N-heterocyclic carbenes.

Language: Английский

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Metal N-heterocyclic carbene complexes as potential metallodrugs in antitumor therapy

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 514, P. 215941 - 215941

Published: May 18, 2024

Language: Английский

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Glycolysis of PET Using 1,3-Dimethylimidazolium-2-Carboxylate as an Organocatalyst

ACS Sustainable Chemistry & Engineering, Journal Year: 2020, Volume and Issue: 8(35), P. 13362 - 13368

Published: Aug. 11, 2020

The use of 1,3-dimethylimidazolium-2-carboxylate as an organocatalyst for the glycolysis waste PET, poly(ethylene terephthalate), is reported first time. Postconsumer PET was completely depolymerized in less than 1 h at 180 °C with up to 60% bis(2-hydroxyethyl terephthalate) (BHET) recovered by precipitation after cooling reaction mixture. Under comparable conditions, basic ionic liquid, 1,3-dimethylimidazolium acetate, a significantly effective catalyst suggesting that catalysis occurs through formation nucleophilic N-heterocyclic carbene.

Language: Английский

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Chemistry of Compounds Based on 1,2,3-Triazolylidene-Type Mesoionic Carbenes

JACS Au, Journal Year: 2021, Volume and Issue: 2(1), P. 22 - 57

Published: Dec. 15, 2021

Mesoionic carbenes (MICs) of the 1,2,3-triazolylidene type have established themselves as a popular class compounds over past decade. Primary reasons for this popularity are their modular synthesis and strong donor properties. While such MICs mostly been used in combination with transition metals, few years also seen utility together main group elements. In paper, we present an overview recent developments on that include, among others, (i) cationic anionic MIC ligands, (ii) donor/acceptor properties these ligands focus several methods known estimating properties, (iii) detailed 3d metal complexes (iv) results redox photophysical based (v) electrocatalysis, redox-switchable catalysis, small-molecule activation to highlight applications contemporary chemistry. By discussing aspects from synthetic, spectroscopic, application point view classes compounds, state art containing perspective future research field.

Language: Английский

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Stable Mesoionic N‐Heterocyclic Olefins (mNHOs)

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(14), P. 5782 - 5787

Published: Dec. 21, 2019

We report a new class of stable mesoionic N-heterocyclic olefins, featuring highly polarized (strongly ylidic) double bond. The ground-state structure cannot be described through an uncharged mesomeric Lewis-structure, thereby structurally distinguishing them from traditional olefins (NHOs). mNHOs can easily obtained deprotonation the corresponding methylated N,N'-diaryl-1,2,3-triazolium and N,N'-diaryl-imidazolium salts, respectively. In their reactivity, they represent strong σ-donor ligands as shown by coordination complexes rhodium boron. Their calculated proton affinities, experimentally derived basicities (competition experiments), well donor abilities (Tolman electronic parameter; TEP) exceed so far reported NHOs.

Language: Английский

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N-Heterocyclic Carbene-Stabilized Germanium and Tin Analogues of Heavier Nitriles: Synthesis, Reactivity, and Catalytic Application

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(37), P. 14576 - 14580

Published: Sept. 3, 2019

The synthesis of stable heavier analogues nitriles as monomeric tetrylene-phosphinidenes MesTerEP(IDipp) (E = Ge, Sn; MesTer 2,6-Mes2C6H3, IDipp C([N-(2,6-iPr2C6H4)CH]2) was achieved by taking advantage NHC (N-heterocyclic carbene, here IDipp) coordination to the low-valent phosphorus center. Multiple bonding character E-P bonds examined experimentally and computationally. Both germanium tin compounds undergo [2+2] cycloaddition with diphenylketene, whereas reaction derivative tris(pentafluorophenyl)borane provided unique "push-pull" phosphastannene (MesTer)(Ar)Sn P(IDipp) (Ar C6F4[B(F)(C6F5)2]). Going further, we demonstrated potential tetrylene-phosphinidene complexes in catalytic hydroboration carbonyl compounds.

Language: Английский

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Recent progress on NHC-stabilized early transition metal (group 3–7) complexes: Synthesis and applications

Coordination Chemistry Reviews, Journal Year: 2020, Volume and Issue: 422, P. 213411 - 213411

Published: July 24, 2020

Language: Английский

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