Literature DB >> 20443633

Synthesis of 4- and 4,5-functionalized imidazol-2-ylidenes from a single 4,5-unsubstituted imidazol-2-ylidene.

Daniel Mendoza-Espinosa1, Bruno Donnadieu, Guy Bertrand.   

Abstract

Using the nucleophilicity of NHCs and aNHCs, as well as the leaving group ability of the former, the carbon-carbon double bond of imidazol-2-ylidenes can be readily mono- and difunctionalized. These results provide also a new light on the formation of abnormal carbene adducts from classical unsaturated NHCs.

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Year:  2010        PMID： 20443633      PMCID： PMC3134311          DOI： 10.1021/ja102639a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  28 in total

1.  Stable Carbenes.

Authors:  Didier Bourissou; Olivier Guerret; François P. Gabbaï; Guy Bertrand
Journal:  Chem Rev       Date:  2000-01-12       Impact factor: 60.622

2.  Investigation of the properties of 4,5-dialkylated N-heterocyclic carbenes.

Authors:  Slawomir Urban; Matyas Tursky; Roland Fröhlich; Frank Glorius
Journal:  Dalton Trans       Date:  2009-07-17       Impact factor: 4.390

3.  Reactivity of electrophilic micro-phosphinidene complexes with N-heterocyclic carbenes: formation of the first main group element adducts of 'abnormal' carbene ligands.

Authors:  Todd W Graham; Konstantin A Udachin; Arthur J Carty
Journal:  Chem Commun (Camb)       Date:  2006-05-18       Impact factor: 6.222

4.  Stabilization of unsymmetrically annelated imidazol-2-ylidenes with respect to their higher group 14 homologues by n-/pi-HOMO inversion.

Authors:  Farman Ullah; Gabor Bajor; Tamas Veszprémi; Peter G Jones; Joachim W Heinicke
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Beyond conventional N-heterocyclic carbenes: abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization.

Authors:  Oliver Schuster; Liangru Yang; Helgard G Raubenheimer; Martin Albrecht
Journal:  Chem Rev       Date:  2009-08       Impact factor: 60.622

6.  Quinone-annulated N-heterocyclic carbene-transition-metal complexes: observation of pi-backbonding using FT-IR spectroscopy and cyclic voltammetry.

Authors:  Matthew D Sanderson; Justin W Kamplain; Christopher W Bielawski
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

7.  Grubbs' ruthenium-carbenes beyond the metathesis reaction: less conventional non-metathetic utility.

Authors:  Benito Alcaide; Pedro Almendros; Amparo Luna
Journal:  Chem Rev       Date:  2009-08       Impact factor: 60.622

8.  Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex.

Authors:  S Gründemann; A Kovacevic; M Albrecht; J W Faller; R H Crabtree
Journal:  Chem Commun (Camb)       Date:  2001-11-07       Impact factor: 6.222

9.  C4-bound imidazolylidenes: from curiosities to high-impact carbene ligands.

Authors:  Martin Albrecht
Journal:  Chem Commun (Camb)       Date:  2008-07-08       Impact factor: 6.222

10.  Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands.

Authors:  Frank Glorius; Gereon Altenhoff; Richard Goddard; Christian Lehmann
Journal:  Chem Commun (Camb)       Date:  2002-11-21       Impact factor: 6.222
View more
  7 in total

1.  Crystalline 1H-1,2,3-triazol-5-ylidenes: new stable mesoionic carbenes (MICs).

Authors:  Gregorio Guisado-Barrios; Jean Bouffard; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-28       Impact factor: 15.336

2.  Deoxyfluorination of phenols.

Authors:  Pingping Tang; Weike Wang; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2011-07-12       Impact factor: 15.419

3.  Synthesis of Highly Stable 1,3-Diaryl-1H-1,2,3-triazol-5-ylidenes and their Applications in Ruthenium-Catalyzed Olefin Metathesis.

Authors:  Jean Bouffard; Benjamin K Keitz; Ralf Tonner; Vincent Lavallo; Gregorio Guisado-Barrios; Gernot Frenking; Robert H Grubbs; Guy Bertrand
Journal:  Organometallics       Date:  2011-03-09       Impact factor: 3.876

4.  A Brief Survey of our Contribution to Stable Carbene Chemistry.

Authors:  David Martin; Mohand Melaimi; Michele Soleilhavoup; Guy Bertrand
Journal:  Organometallics       Date:  2011-09-22       Impact factor: 3.876

5.  Facile preparation of homo- and hetero-dimetallic complexes with a 4-phosphino-substituted NHC ligand. Toward the design of multifunctional catalysts.

Authors:  Daniel Mendoza-Espinosa; Bruno Donnadieu; Guy Bertrand
Journal:  Chem Asian J       Date:  2011-02-14

Review 6.  Functionalised N-Heterocyclic Carbene Ligands in Bimetallic Architectures.

Authors:  Kieren J Evans; Stephen M Mansell
Journal:  Chemistry       Date:  2020-03-18       Impact factor: 5.236

7.  PhenoFluor: Practical Synthesis, New Formulation, and Deoxyfluorination of Heteroaromatics.

Authors:  Teppei Fujimoto; Fabian Becker; Tobias Ritter
Journal:  Org Process Res Dev       Date:  2014-07-23       Impact factor: 3.317
  7 in total

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