Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Nonproductive events in ring-closing metathesis using ruthenium catalysts.

Literature DB >> 20518557

Nonproductive events in ring-closing metathesis using ruthenium catalysts.

Ian C Stewart¹, Benjamin K Keitz, Kevin M Kuhn, Renee M Thomas, Robert H Grubbs.

Abstract

The relative TONs of productive and nonproductive metathesis reactions of diethyl diallylmalonate are compared for eight different ruthenium-based catalysts. Nonproductive cross metathesis is proposed to involve a chain-carrying ruthenium methylidene. A second more-challenging substrate (dimethyl allylmethylallylmalonate) that forms a trisubstituted olefin product is used to further delineate the effect of catalyst structure on the relative efficiencies of these processes. A steric model is proposed to explain the observed trends.

Entities: Chemical Gene

Mesh：

Substances：
Alkenes
Ruthenium

Year: 2010 PMID： 20518557 PMCID： PMC2908527 DOI： 10.1021/ja1029045

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

8 in total

1. Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-01 Impact factor: 15.336

2. Metathesis reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

Review 3. The remarkable metal-catalysed olefin metathesis reaction.

Authors: Amir H Hoveyda; Adil R Zhugralin
Journal: Nature Date: 2007-11-08 Impact factor: 49.962

4. Synthesis and reactivity of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbenes.

Authors: Donde R Anderson; Vincent Lavallo; Daniel J O'Leary; Guy Bertrand; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors: M Scholl; S Ding; C W Lee; R H Grubbs
Journal: Org Lett Date: 1999-09-23 Impact factor: 6.005

6. Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

Authors: Ian C Stewart; Thay Ung; Alexandre A Pletnev; Jacob M Berlin; Robert H Grubbs; Yann Schrodi
Journal: Org Lett Date: 2007-03-23 Impact factor: 6.005

7. Effects of NHC-backbone substitution on efficiency in ruthenium-based olefin metathesis.

Authors: Kevin M Kuhn; Jean-Baptiste Bourg; Cheol K Chung; Scott C Virgil; Robert H Grubbs
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

8. The significance of degenerate processes to enantioselective olefin metathesis reactions promoted by stereogenic-at-Mo complexes.

Authors: Simon J Meek; Steven J Malcolmson; Bo Li; Richard R Schrock; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-11-18 Impact factor: 15.419

8 in total

12 in total

1. Highly selective ruthenium metathesis catalysts for ethenolysis.

Authors: Renee M Thomas; Benjamin K Keitz; Timothy M Champagne; Robert H Grubbs
Journal: J Am Chem Soc Date: 2011-04-21 Impact factor: 15.419

2. Probing the origin of degenerate metathesis selectivity via characterization and dynamics of ruthenacyclobutanes containing variable NHCs.

Authors: Benjamin K Keitz; Robert H Grubbs
Journal: J Am Chem Soc Date: 2011-09-15 Impact factor: 15.419

Nonproductive events in ring-closing metathesis using ruthenium catalysts.

1. Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

2. Metathesis reactions in total synthesis.

Review 3. The remarkable metal-catalysed olefin metathesis reaction.

4. Synthesis and reactivity of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbenes.

5. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

6. Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

7. Effects of NHC-backbone substitution on efficiency in ruthenium-based olefin metathesis.

8. The significance of degenerate processes to enantioselective olefin metathesis reactions promoted by stereogenic-at-Mo complexes.

1. Highly selective ruthenium metathesis catalysts for ethenolysis.

2. Probing the origin of degenerate metathesis selectivity via characterization and dynamics of ruthenacyclobutanes containing variable NHCs.

3. Allylmalonate as an activator subunit for the initiation of relay ring-closing metathesis reactions.

4. Z-selective homodimerization of terminal olefins with a ruthenium metathesis catalyst.

5. Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis.

6. Improved ruthenium catalysts for Z-selective olefin metathesis.

Review 7. Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.

8. Toward a simulation approach for alkene ring-closing metathesis: scope and limitations of a model for RCM.

9. Hoveyda-Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15.

10. Consequences of the electronic tuning of latent ruthenium-based olefin metathesis catalysts on their reactivity.