Origin paper
N-heterocyclic carbenes: organocatalysts with moderate nucleophilicity but extraordinarily high Lewis basicity.
N‐Heterocyclische Carbene: Organokatalysatoren mit mäßiger Nucleophilie, aber außerordentlich hoher Lewis‐Basizität
Nucleophilic reactivities of deoxy Breslow intermediates: how does aromaticity affect the catalytic activities of N-heterocyclic carbenes?
Nucleophile Reaktivitäten von Desoxy-Breslow-Intermediaten: Wie beeinflusst Aromatizität die katalytische Aktivität N-heterocyclischer Carbene?†
Structures and reactivities of O-methylated Breslow intermediates.
Struktur und Reaktivität O‐methylierter Breslow‐Intermediate
On new N-heterocyclic carbene derived alkylidene imidazolines.
N-heterocyclic carbene catalyzed umpolung of Michael acceptors for intermolecular reactions.
Aldehyde umpolung by N-heterocyclic carbenes: NMR characterization of the Breslow intermediate in its keto form, and a spiro-dioxolane as the resting state of the catalytic system.
Experimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene.
Umpolung von Aldehyden mit N-heterocyclischen Carbenen: NMR-Charakterisierung des Breslow-Intermediats in seiner Ketoform und eines Spirodioxolans als “resting state” des katalytischen Systems†
Organocatalytic tail-to-tail dimerization of olefin: umpolung of methyl methacrylate mediated by N-heterocyclic carbene.
N-heterocyclic carbene catalyzed umpolung of styrenes: mechanistic elucidation and selective tail-to-tail dimerization.
The effect of the N-mesityl group in NHC-catalyzed reactions.
Umpolung by N-heterocyclic carbenes: generation and reactivity of the elusive 2,2-diamino enols (Breslow intermediates).
Conjugate-addition organopolymerization: rapid production of acrylic bioplastics by N-heterocyclic carbenes.
Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes.
Isolable analogues of the Breslow intermediate derived from chiral triazolylidene carbenes.
On the organocatalytic activity of N-heterocyclic carbenes: role of sulfur in thiamine.
Nucleophilic addition of enols and enamines to α,β-unsaturated acyl azoliums: mechanistic studies.
Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.
Umpolung mit N‐heterocyclischen Carbenen: Generierung und Reaktivität von Breslow‐Intermediaten (2,2‐Diaminoenole)
Cooperative N-heterocyclic carbene/Brønsted acid catalysis for the tail-to-tail (co)dimerization of methacrylonitrile.
On the Involvement of a Spiroepoxide Intermediate in N‐Heterocyclic Carbene (NHC)‐Catalyzed Benzoin Condensations – An Approach by Oxygenation of Deoxy‐Breslow Intermediates
Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent.
Nukleophile Addition von Enolen und Enaminen an α,β‐ungesättigte Acylazoliumionen: Mechanistische Studien
Proton transfer reactions of triazol-3-ylidenes: kinetic acidities and carbon acid pKa values for twenty triazolium salts in aqueous solution.
Sequential one-pot and three-component reactions of an N -heterocyclic carbene to form 4-(1,2,4-triazol-5-ylidene)pyrrolidine-2,5-diones: a tandem umpolung/annulation sequence via deoxy-Breslow intermediates
N-Heterocyclic carbene-catalyzed cyclotetramerization of acrylates.
Durch ein N‐heterocyclisches Carben katalysierte Umpolung von Michael‐Akzeptoren für intermolekulare Reaktionen
Proton-transfer polymerization (HTP): converting methacrylates to polyesters by an N-heterocyclic carbene.
Characterization of the key intermediates of carbene-catalyzed umpolung by NMR spectroscopy and X-ray diffraction: breslow intermediates, homoenolates, and azolium enolates.
Organocatalytic conjugate-addition polymerization of linear and cyclic acrylic monomers by N-heterocyclic carbenes: mechanisms of chain initiation, propagation, and termination.
Preparation of 2‐Alkylidene‐Substituted 1,3,4,5‐Tetramethylimidazolines and Their Reactivity Towards RhI Complexes and B(C6F5)3
Dual Activation in N-Heterocyclic Carbene-Organocatalysis
N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.
Charakterisierung der Schlüsselintermediate von carbenkatalysierten Umpolungen durch Kristallstrukturanalyse/NMR-Spektroskopie: Breslow-Intermediate, Homoenolate und Azoliumenolate†
Extending NHC-catalysis: coupling aldehydes with unconventional reaction partners.
The measure of all rings--N-heterocyclic carbenes.
Quantitative Treatments of Nucleophilicity and Carbon Lewis Basicity
pKas of the conjugate acids of N-heterocyclic carbenes in water.
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20062016
The measure of all rings--N-heterocyclic carbenes.Extending NHC-catalysis: coupling aldehydes with unconventional reaction partners.Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.N-heterocyclic carbene catalyzed umpolung of Michael acceptors for intermolecular reactions.N-heterocyclic carbenes: organocatalysts with moderate nucleophilicity but extraordinarily high Lewis basicity.The effect of the N-mesityl group in NHC-catalyzed reactions.Organocatalytic tail-to-tail dimerization of olefin: umpolung of methyl methacrylate mediated by N-heterocyclic carbene.Dual Activation in N-Heterocyclic Carbene-OrganocatalysisUmpolung by N-heterocyclic carbenes: generation and reactivity of the elusive 2,2-diamino enols (Breslow intermediates).Proton transfer reactions of triazol-3-ylidenes: kinetic acidities and carbon acid pKa values for twenty triazolium salts in aqueous solution.Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent.pKas of the conjugate acids of N-heterocyclic carbenes in water.Isolable analogues of the Breslow intermediate derived from chiral triazolylidene carbenes.Aldehyde umpolung by N-heterocyclic carbenes: NMR characterization of the Breslow intermediate in its keto form, and a spiro-dioxolane as the resting state of the catalytic system.Conjugate-addition organopolymerization: rapid production of acrylic bioplastics by N-heterocyclic carbenes.Characterization of the key intermediates of carbene-catalyzed umpolung by NMR spectroscopy and X-ray diffraction: breslow intermediates, homoenolates, and azolium enolates.Nucleophilic reactivities of deoxy Breslow intermediates: how does aromaticity affect the catalytic activities of N-heterocyclic carbenes?Nucleophilic addition of enols and enamines to α,β-unsaturated acyl azoliums: mechanistic studies.Organocatalytic conjugate-addition polymerization of linear and cyclic acrylic monomers by N-heterocyclic carbenes: mechanisms of chain initiation, propagation, and termination.N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.Structures and reactivities of O-methylated Breslow intermediates.On the organocatalytic activity of N-heterocyclic carbenes: role of sulfur in thiamine.On new N-heterocyclic carbene derived alkylidene imidazolines.Preparation of 2‐Alkylidene‐Substituted 1,3,4,5‐Tetramethylimidazolines and Their Reactivity Towards RhI Complexes and B(C6F5)3Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes.N-heterocyclic carbene catalyzed umpolung of styrenes: mechanistic elucidation and selective tail-to-tail dimerization.N‐Heterocyclische Carbene: Organokatalysatoren mit mäßiger Nucleophilie, aber außerordentlich hoher Lewis‐BasizitätExperimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene.Umpolung mit N‐heterocyclischen Carbenen: Generierung und Reaktivität von Breslow‐Intermediaten (2,2‐Diaminoenole)Proton-transfer polymerization (HTP): converting methacrylates to polyesters by an N-heterocyclic carbene.Cooperative N-heterocyclic carbene/Brønsted acid catalysis for the tail-to-tail (co)dimerization of methacrylonitrile.Umpolung von Aldehyden mit N-heterocyclischen Carbenen: NMR-Charakterisierung des Breslow-Intermediats in seiner Ketoform und eines Spirodioxolans als “resting state” des katalytischen Systems†Durch ein N‐heterocyclisches Carben katalysierte Umpolung von Michael‐Akzeptoren für intermolekulare ReaktionenNucleophile Reaktivitäten von Desoxy-Breslow-Intermediaten: Wie beeinflusst Aromatizität die katalytische Aktivität N-heterocyclischer Carbene?†N-Heterocyclic carbene-catalyzed cyclotetramerization of acrylates.Charakterisierung der Schlüsselintermediate von carbenkatalysierten Umpolungen durch Kristallstrukturanalyse/NMR-Spektroskopie: Breslow-Intermediate, Homoenolate und Azoliumenolate†Sequential one-pot and three-component reactions of an N -heterocyclic carbene to form 4-(1,2,4-triazol-5-ylidene)pyrrolidine-2,5-diones: a tandem umpolung/annulation sequence via deoxy-Breslow intermediatesNukleophile Addition von Enolen und Enaminen an α,β‐ungesättigte Acylazoliumionen: Mechanistische StudienStruktur und Reaktivität O‐methylierter Breslow‐IntermediateOn the Involvement of a Spiroepoxide Intermediate in N‐Heterocyclic Carbene (NHC)‐Catalyzed Benzoin Condensations – An Approach by Oxygenation of Deoxy‐Breslow IntermediatesQuantitative Treatments of Nucleophilicity and Carbon Lewis BasicityDröge, 2010Biju, 2011Fischer, 2006Biju, 2011Maji, 2011Mahatthananchai, 2012Matsuoka, 2011Hirano, 2011Berkessel, 2012Massey, 2012Collett, 2013Higgins, 2011DiRocco, 2012Berkessel, 2010Zhang, 2012Berkessel, 2013Maji, 2012Samanta, 2012Zhang, 2013Atienza, 2011Maji, 2012Hollóczki, 2012Knappke, 2010Kronig, 2013Levens, 2016Schedler, 2014Maji, 2011Kato, 2013Berkessel, 2012Hong, 2014Kato, 2014Berkessel, 2010Biju, 2011Maji, 2012Matsuoka, 2013Berkessel, 2013Matsuoka, 2012Samanta, 2012Maji, 2012Berkessel, 2014Lakhdar, 2016Dröge, 2010Biju, 2011Fischer, 2006Biju, 2011Maji, 2011Mahatthananchai, 2012Matsuoka, 2011Hirano, 2011Berkessel, 2012Massey, 2012Collett, 2013Higgins, 2011DiRocco, 2012Berkessel, 2010Zhang, 2012Berkessel, 2013Maji, 2012Samanta, 2012Zhang, 2013Atienza, 2011Maji, 2012Hollóczki, 2012Knappke, 2010Kronig, 2013Levens, 2016Schedler, 2014Maji, 2011Kato, 2013Berkessel, 2012Hong, 2014Kato, 2014Berkessel, 2010Biju, 2011Maji, 2012Matsuoka, 2013Berkessel, 2013Matsuoka, 2012Samanta, 2012Maji, 2012Berkessel, 2014Lakhdar, 2016
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Since the first isolation and characterization of stable Nheterocyclic carbenes (NHCs) by Arduengo and co-workers in 1991, these compounds have attracted great interest in various fields of chemistry. As molecules with divalent carbon atoms, NHCs (e.g., 1–3, Scheme 1) are not only of theoretical interest but also of practical relevance as ligands in metal complexes and as nucleophilic organocatalysts.