Literature DB >> 21603126

Ruthenium Olefin Metathesis Catalysts Bearing Carbohydrate-Based N-Heterocyclic Carbenes.

Benjamin K Keitz1, Robert H Grubbs.   

Abstract

Ru-based olefin metathesis catalysts containing carbohydrate-derived NHCs from glucose and galactose were synthesized and characterized by NMR spectroscopy. 2D-NMR spectroscopy revealed the presence of Ru-C (benzylidene) rotamers at RT and the rate of rotation was measured using magnetization transfer and VT-NMR spectroscopy. The catalysts were found to be effective at ring-opening metathesis polymerization (ROMP), ring closing metathesis (RCM), cross metathesis (CM), and asymmetric ring opening cross metathesis (AROCM) and showed surprising selectivity in both CM and AROCM.

Entities:  

Year:  2010        PMID： 21603126      PMCID： PMC3097126          DOI： 10.1021/om900864r

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  25 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.  Carbohydrate complexes of platinum-group metals.

Authors:  D Steinborn; H Junicke
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

3.  Chiral Ru-based complexes for asymmetric olefin metathesis: enhancement of catalyst activity through steric and electronic modifications.

Authors:  Joshua J Van Veldhuizen; Dennis G Gillingham; Steven B Garber; Osamu Kataoka; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

Review 4.  Ligands derived from carbohydrates for asymmetric catalysis.

Authors:  Montserrat Diéguez; Oscar Pàmies; Carmen Claver
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

5.  Double C--H activation of an N-heterocyclic carbene ligand in a ruthenium olefin metathesis catalyst.

Authors:  Soon Hyeok Hong; Anatoly Chlenov; Michael W Day; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 6.  Glycoprotein synthesis: an update.

Authors:  David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

7.  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

Review 8.  The chemical neurobiology of carbohydrates.

Authors:  Heather E Murrey; Linda C Hsieh-Wilson
Journal:  Chem Rev       Date:  2008-05-02       Impact factor: 60.622

9.  Olefin metathesis catalyst: stabilization effect of backbone substitutions of N-heterocyclic carbene.

Authors:  Cheol K Chung; Robert H Grubbs
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005

10.  Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis.

Authors:  Timothy W Funk; Jacob M Berlin; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419
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  5 in total

1.  Characterization and dynamics of substituted ruthenacyclobutanes relevant to the olefin cross-metathesis reaction.

Authors:  Anna G Wenzel; Garrett Blake; David G VanderVelde; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-03-31       Impact factor: 15.419

2.  Galactopyranoside-Substituted N-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Stability, and Catalytic Applications to Alkyne Hydration.

Authors:  Ariana W Hobsteter; Mercedes A Badajoz; Marcos J Lo Fiego; Gustavo F Silbestri
Journal:  ACS Omega       Date:  2022-06-14

3.  Light-induced olefin metathesis.

Authors:  Yuval Vidavsky; N Gabriel Lemcoff
Journal:  Beilstein J Org Chem       Date:  2010-11-23       Impact factor: 2.883

4.  Carbohydrate-Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction.

Authors:  Joseph P Byrne; Lidia Delgado; Francesca Paradisi; Martin Albrecht
Journal:  ChemCatChem       Date:  2022-03-11       Impact factor: 5.497

Review 5.  Carbohydrates as enantioinduction components in stereoselective catalysis.

Authors:  Alexander S Henderson; John F Bower; M Carmen Galan
Journal:  Org Biomol Chem       Date:  2016-04-26       Impact factor: 3.876
  5 in total

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