Literature DB >> 21649443

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

Benjamin K Keitz1, Koji Endo, Myles B Herbert, Robert H Grubbs.   

Abstract

The cross-metathesis of terminal olefins using a novel ruthenium catalyst results in excellent selectivity for the Z-olefin homodimer. The reaction was found to tolerate a large number of functional groups, solvents, and temperatures while maintaining excellent Z-selectivity, even at high reaction conversions.

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Year:  2011        PMID： 21649443      PMCID： PMC3138429          DOI： 10.1021/ja203488e

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


  23 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

Review 2.  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

3.  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

4.  Mechanistic insights into the ruthenium-catalysed diene ring-closing metathesis reaction.

Authors:  Edwin F van der Eide; Warren E Piers
Journal:  Nat Chem       Date:  2010-05-09       Impact factor: 24.427

5.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

6.  Synthesis of fluorine-18 functionalized nanoparticles for use as in vivo molecular imaging agents.

Authors:  John B Matson; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2008-05-02       Impact factor: 15.419

7.  Well-defined liquid crystal gels from telechelic polymers.

Authors:  Yan Xia; Rafael Verduzco; Robert H Grubbs; Julia A Kornfield
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

8.  Comparison of Ru- and Mo-based chiral olefin metathesis catalysts. Complementarity in asymmetric ring-opening/cross-metathesis reactions of oxa- and azabicycles.

Authors:  G Alex Cortez; Carl A Baxter; Richard R Schrock; Amir H Hoveyda
Journal:  Org Lett       Date:  2007-06-22       Impact factor: 6.005

9.  Highly Z-selective metathesis homocoupling of terminal olefins.

Authors:  Annie J Jiang; Yu Zhao; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

10.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962
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  27 in total

1.  Traceless Protection for More Broadly Applicable Olefin Metathesis.

Authors:  Yucheng Mu; Thach T Nguyen; Farid W van der Mei; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-13       Impact factor: 15.336

2.  High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis.

Authors:  Ming Joo Koh; R Kashif M Khan; Sebastian Torker; Miao Yu; Malte S Mikus; Amir H Hoveyda
Journal:  Nature       Date:  2015-01-08       Impact factor: 49.962

3.  Ru-Based Z-Selective Metathesis Catalysts with Modified Cyclometalated Carbene Ligands.

Authors:  Sarah M Bronner; Myles B Herbert; Paresma R Patel; Vanessa M Marx; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-10       Impact factor: 9.825

4.  Concise syntheses of insect pheromones using Z-selective cross metathesis.

Authors:  Myles B Herbert; Vanessa M Marx; Richard L Pederson; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-10       Impact factor: 15.336

5.  Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols.

Authors:  Peter K Dornan; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-27       Impact factor: 15.336

6.  Z-Selective Ruthenium Metathesis Catalysts: Comparison of Nitrate and Nitrite X-type Ligands.

Authors:  Melanie A Pribisko; Tonia S Ahmed; Robert H Grubbs
Journal:  Polyhedron       Date:  2014-12-14       Impact factor: 3.052

7.  Synthesis of Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds through stereoselective catalytic cross-metathesis.

Authors:  Elizabeth T Kiesewetter; Robert V O'Brien; Elsie C Yu; Simon J Meek; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2013-04-15       Impact factor: 15.419

8.  Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.

Authors:  Vanessa M Marx; Myles B Herbert; Benjamin K Keitz; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2012-12-21       Impact factor: 15.419

9.  Highly active ruthenium metathesis catalysts exhibiting unprecedented activity and Z-selectivity.

Authors:  Lauren E Rosebrugh; Myles B Herbert; Vanessa M Marx; Benjamin K Keitz; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

10.  Reactivation of a Ruthenium-Based Olefin Metathesis Catalyst.

Authors:  Daniel S Tabari; Daniel R Tolentino; Yann Schrodi
Journal:  Organometallics       Date:  2012-12-21       Impact factor: 3.876
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