N-heterocyclic carbenes: organocatalysts with moderate nucleophilicity but extraordinarily high Lewis basicity.
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Origin paper
N-heterocyclic carbenes: organocatalysts with moderate nucleophilicity but extraordinarily high Lewis basicity.
B. Maji, M. Breugst, H. Mayr
2011
N‐Heterocyclische Carbene: Organokatalysatoren mit mäßiger Nucleophilie, aber außerordentlich hoher Lewis‐Basizität
Biplab Maji, Martin Breugst, Herbert Mayr
2011
Nucleophilic reactivities of deoxy Breslow intermediates: how does aromaticity affect the catalytic activities of N-heterocyclic carbenes?
B. Maji, M. Horn, H. Mayr
2012
Nucleophile Reaktivitäten von Desoxy-Breslow-Intermediaten: Wie beeinflusst Aromatizität die katalytische Aktivität N-heterocyclischer Carbene?†
Biplab Maji, M. Horn, Herbert Mayr
2012
Structures and reactivities of O-methylated Breslow intermediates.
B. Maji, H. Mayr
2012
Struktur und Reaktivität O‐methylierter Breslow‐Intermediate
Biplab Maji, Herbert Mayr
2012
On new N-heterocyclic carbene derived alkylidene imidazolines.
Christiane E. I. Knappke, J. Neudörfl, A. J. von Wangelin
2010
N-heterocyclic carbene catalyzed umpolung of Michael acceptors for intermolecular reactions.
A. Biju, Mohan Padmanaban, N. Wurz, F. Glorius
2011
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.
A. Berkessel, Silvia Elfert, Kerstin Etzenbach‐Effers, J. Teles
2010
Experimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene.
Terumasa Kato, Yoshiya Ota, S. Matsuoka, Koji Takagi, Masato Suzuki
2013
Umpolung von Aldehyden mit N-heterocyclischen Carbenen: NMR-Charakterisierung des Breslow-Intermediats in seiner Ketoform und eines Spirodioxolans als “resting state” des katalytischen Systems†
A. Berkessel, Silvia Elfert, Kerstin Etzenbach‐Effers, J. H. Teles
2010
Organocatalytic tail-to-tail dimerization of olefin: umpolung of methyl methacrylate mediated by N-heterocyclic carbene.
S. Matsuoka, Yoshiya Ota, Atsushi Washio, Akiho Katada, K. Ichioka, Koji Takagi, Masato Suzuki
2011
N-heterocyclic carbene catalyzed umpolung of styrenes: mechanistic elucidation and selective tail-to-tail dimerization.
M. Schedler, N. Wurz, C. Daniliuc, F. Glorius
2014
The effect of the N-mesityl group in NHC-catalyzed reactions.
J. Mahatthananchai, J. Bode
2012
Umpolung by N-heterocyclic carbenes: generation and reactivity of the elusive 2,2-diamino enols (Breslow intermediates).
A. Berkessel, Silvia Elfert, V. Yatham, J. Neudörfl, Nils E. Schlörer, J. Henrique Teles
2012
Conjugate-addition organopolymerization: rapid production of acrylic bioplastics by N-heterocyclic carbenes.
Yuetao Zhang, E. Chen
2012
Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes.
A. Levens, Feng An, M. Breugst, H. Mayr, D. Lupton
2016
Isolable analogues of the Breslow intermediate derived from chiral triazolylidene carbenes.
D. DiRocco, K. Oberg, T. Rovis
2012
On the organocatalytic activity of N-heterocyclic carbenes: role of sulfur in thiamine.
Oldamur Hollóczki, Z. Kelemen, L. Nyulászi
2012
Nucleophilic addition of enols and enamines to α,β-unsaturated acyl azoliums: mechanistic studies.
Ramesh C. Samanta, B. Maji, Suman De Sarkar, K. Bergander, R. Fröhlich, Christian Mück‐Lichtenfeld, H. Mayr, A. Studer
2012
Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.
C. Fischer, S. Smith, D. Powell, G. C. Fu
2006
Umpolung mit N‐heterocyclischen Carbenen: Generierung und Reaktivität von Breslow‐Intermediaten (2,2‐Diaminoenole)
A. Berkessel, Silvia Elfert, V. R. Yatham, Jörg‐M. Neudörfl, Nils E. Schlörer, J. H. Teles
2012
Cooperative N-heterocyclic carbene/Brønsted acid catalysis for the tail-to-tail (co)dimerization of methacrylonitrile.
Terumasa Kato, S. Matsuoka, Masato Suzuki
2014
On the Involvement of a Spiroepoxide Intermediate in N‐Heterocyclic Carbene (NHC)‐Catalyzed Benzoin Condensations – An Approach by Oxygenation of Deoxy‐Breslow Intermediates
A. Berkessel, Silvia Elfert
2014
Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent.
Christopher J. Collett, Richard S. Massey, Oliver R. Maguire, A. Batsanov, A. O’Donoghue, Andrew D. Smith
2013
Nukleophile Addition von Enolen und Enaminen an α,β‐ungesättigte Acylazoliumionen: Mechanistische Studien
Ramesh C. Samanta, B. Maji, S. Sarkar, K. Bergander, R. Fröhlich, Christian Mück‐Lichtenfeld, H. Mayr, A. Studer
2012
Proton transfer reactions of triazol-3-ylidenes: kinetic acidities and carbon acid pKa values for twenty triazolium salts in aqueous solution.
Richard S. Massey, Christopher J. Collett, Anita G. Lindsay, Andrew D. Smith, A. O’Donoghue
2012
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
S. Matsuoka, Yusuke Tochigi, Koji Takagi, Masato Suzuki
2012
N-Heterocyclic carbene-catalyzed cyclotetramerization of acrylates.
S. Matsuoka, Shoko Namera, Atsushi Washio, Koji Takagi, Masato Suzuki
2013
Durch ein N‐heterocyclisches Carben katalysierte Umpolung von Michael‐Akzeptoren für intermolekulare Reaktionen
Akkattu T. Biju, Mohan Padmanaban, Nathalie E. Wurz, F. Glorius
2011
Proton-transfer polymerization (HTP): converting methacrylates to polyesters by an N-heterocyclic carbene.
Miao Hong, E. Chen
2014
Characterization of the key intermediates of carbene-catalyzed umpolung by NMR spectroscopy and X-ray diffraction: breslow intermediates, homoenolates, and azolium enolates.
A. Berkessel, V. Yatham, Silvia Elfert, J. Neudörfl
2013
Organocatalytic conjugate-addition polymerization of linear and cyclic acrylic monomers by N-heterocyclic carbenes: mechanisms of chain initiation, propagation, and termination.
Yuetao Zhang, M. Schmitt, L. Falivene, L. Caporaso, L. Cavallo, E. Chen
2013
Preparation of 2‐Alkylidene‐Substituted 1,3,4,5‐Tetramethylimidazolines and Their Reactivity Towards RhI Complexes and B(C6F5)3
Sabrina Kronig, P. Jones, M. Tamm
2013
Dual Activation in N-Heterocyclic Carbene-Organocatalysis
Keiichi Hirano, Isabel Piel, F. Glorius
2011
N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.
Roxanne L. Atienza, H. Roth, K. Scheidt
2011
Charakterisierung der Schlüsselintermediate von carbenkatalysierten Umpolungen durch Kristallstrukturanalyse/NMR-Spektroskopie: Breslow-Intermediate, Homoenolate und Azoliumenolate†
A. Berkessel, V. R. Yatham, Silvia Elfert, Jörg‐M. Neudörfl
2013
Extending NHC-catalysis: coupling aldehydes with unconventional reaction partners.
A. Biju, N. Kuhl, F. Glorius
2011
The measure of all rings--N-heterocyclic carbenes.
T. Dröge, F. Glorius
2010
Quantitative Treatments of Nucleophilicity and Carbon Lewis Basicity
S. Lakhdar
2016
pKas of the conjugate acids of N-heterocyclic carbenes in water.
E. M. Higgins, J. Sherwood, Anita G. Lindsay, James Armstrong, Richard S. Massey, R. Alder, A. O’Donoghue
2011
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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.