Literature DB >> 23317178

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

Lauren E Rosebrugh1, Myles B Herbert, Vanessa M Marx, Benjamin K Keitz, Robert H Grubbs.   

Abstract

A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6-diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (>95%), as well as unparalleled TONs of up to 7400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically active species were synthesized using an improved method employing sodium carboxylates to induce the salt metathesis and C-H activation of these chelated complexes. All of these new ruthenium-based catalysts are highly Z-selective in the homodimerization of terminal olefins.

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Year:  2013        PMID: 23317178      PMCID: PMC3561903          DOI: 10.1021/ja311916m

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

2.  Z-Selectivity in olefin metathesis with chelated Ru catalysts: computational studies of mechanism and selectivity.

Authors:  Peng Liu; Xiufang Xu; Xiaofei Dong; Benjamin K Keitz; Myles B Herbert; Robert H Grubbs; K N Houk
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

Review 3.  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

4.  Chelated ruthenium catalysts for Z-selective olefin metathesis.

Authors:  Koji Endo; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

5.  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

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

Authors:  Benjamin K Keitz; Koji Endo; Myles B Herbert; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-06-08       Impact factor: 15.419

7.  Cis-selective ring-opening metathesis polymerization with ruthenium catalysts.

Authors:  Benjamin K Keitz; Alexey Fedorov; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2012-01-20       Impact factor: 15.419

8.  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

9.  Z-selective olefin metathesis processes catalyzed by a molybdenum hexaisopropylterphenoxide monopyrrolide complex.

Authors:  Margaret M Flook; Annie J Jiang; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-06-17       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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  29 in total

1.  Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors:  Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       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.  Alkene chemoselectivity in ruthenium-catalyzed Z-selective olefin metathesis.

Authors:  Jeffrey S Cannon; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

5.  Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.

Authors:  Hanbin Lee; Manoj V Mane; Ho Ryu; Debashis Sahu; Mu-Hyun Baik; Chae S Yi
Journal:  J Am Chem Soc       Date:  2018-08-03       Impact factor: 15.419

6.  Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins.

Authors:  Yiyang Liu; Kelly E Kim; Myles B Herbert; Alexey Fedorov; Robert H Grubbs; Brian M Stoltz
Journal:  Adv Synth Catal       Date:  2014-01-01       Impact factor: 5.837

7.  Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

Authors:  John Hartung; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

8.  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

9.  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

10.  Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins.

Authors:  Peter K Dornan; Daniel Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2016-05-11       Impact factor: 15.419

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