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Literature DB >> 21574621

Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis.

Benjamin K Keitz¹, Jean Bouffard, Guy Bertrand, Robert H Grubbs.

Abstract

The synthesis of a ruthenium complex containing an N-heterocylic carbene (NHC) and a mesoionic carbene (MIC) is described wherein addition of a Brønsted acid results in protonolysis of the Ru-MIC bond to generate an extremely active metathesis catalyst. Mechanistic studies implicated a rate-determining protonation step in the generation of the metathesis-active species. The activity of the NHC/MIC catalyst was found to exceed those of current commercial ruthenium catalysts.

Entities: Chemical Disease Species

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Year: 2011 PMID： 21574621 PMCID： PMC3121189 DOI： 10.1021/ja203070r

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

21 in total

1. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors: T M Trnka; R H Grubbs
Journal: Acc Chem Res Date: 2001-01 Impact factor: 22.384

2. Mechanism and activity of ruthenium olefin metathesis catalysts.

Authors: M S Sanford; J A Love; R H Grubbs
Journal: J Am Chem Soc Date: 2001-07-11 Impact factor: 15.419

3. Solvation states of HCl in mixed ether:acid crystals: a computational study.

Authors: V Buch; F Mohamed; Mathias Krack; J Sadlej; J P Devlin; M Parrinello
Journal: J Chem Phys Date: 2004-12-22 Impact factor: 3.488

4. 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

5. [(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings.

Authors: Silvia Díez-González; Steven P Nolan
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 6. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Authors: Georgios C Vougioukalakis; Robert H Grubbs
Journal: Chem Rev Date: 2010-03-10 Impact factor: 60.622

Review 7. Latent olefin metathesis catalysts.

Authors: Stijn Monsaert; Ana Lozano Vila; Renata Drozdzak; Pascal Van Der Voort; Francis Verpoort
Journal: Chem Soc Rev Date: 2009-09-23 Impact factor: 54.564

8. 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

9. Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions.

Authors: Soon Hyeok Hong; Michael W Day; Robert H Grubbs
Journal: J Am Chem Soc Date: 2004-06-23 Impact factor: 15.419

10. Reversible inhibition/activation of olefin metathesis: a kinetic investigation of ROMP and RCM reactions with Grubbs' catalyst.

Authors: Steven J P'Pool; Hans-Jörg Schanz
Journal: J Am Chem Soc Date: 2007-10-27 Impact factor: 15.419

8 in total

8. Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities.

Authors: Carmen Mejuto; Beatriz Royo; Gregorio Guisado-Barrios; Eduardo Peris
Journal: Beilstein J Org Chem Date: 2015-12-14 Impact factor: 2.883

8 in total

Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis.

1. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

2. Mechanism and activity of ruthenium olefin metathesis catalysts.

3. Solvation states of HCl in mixed ether:acid crystals: a computational study.

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

5. [(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings.

Review 6. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Review 7. Latent olefin metathesis catalysts.

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

9. Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions.

10. Reversible inhibition/activation of olefin metathesis: a kinetic investigation of ROMP and RCM reactions with Grubbs' catalyst.

1. Structurally Characterized Cationic Silver(I) and Ruthenium(II)carbene complexes of 1,2,3-Triazol-5-ylidenes.

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

3. A Ruthenium Catalyst for Olefin Metathesis Featuring an Anti-Bredt N-Heterocyclic Carbene Ligand.

4. Mesoionic thiazol-5-ylidenes as ligands for transition metal complexes.

5. Bis(1,2,3-triazol-5-ylidenes) (i-bitz) as Stable 1,4-Bidentate Ligands Based on Mesoionic Carbenes (MICs).

6. Latent ruthenium-indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand.

Review 7. Chemistry of Compounds Based on 1,2,3-Triazolylidene-Type Mesoionic Carbenes.

8. Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities.