Onium-tagged Ru complexes as universal catalysts for olefin metathesis reactions in various media

2009 ◽  
Vol 81 (11) ◽  
pp. 2001-2012 ◽  
Author(s):  
Łukasz Gułajski ◽  
Marc Mauduit ◽  
Karol Grela
Keyword(s):  
Olefin Metathesis ◽  
Methylene Chloride ◽  
Enyne Metathesis ◽  
Traditional Media ◽  
Neat Water ◽  
Alcohol Water ◽  
Metathesis Reactions ◽  
Ru Complexes ◽  
Metathesis Catalysts ◽  
Aqueous Conditions

Polar olefin metathesis catalysts bearing a pendant electron-withdrawing (EWG) onium group are reviewed. The presence of this group not only activates the catalysts electronically, but renders them more hydrophilic. Catalysts can, therefore, be efficiently used not only in traditional media such as methylene chloride and toluene, but also in technical-grade alcohols, alcohol–water mixtures, and in neat water. In addition, some onium-tagged catalysts can act as inisurfs (initiator + surfactant molecules), promoting metathesis under heterogeneous aqueous conditions. Finally, some of these catalysts can be used in ionic liquids. Various ring-closing-, cross- and enyne metathesis reactions were conducted with these catalysts.

scholarly journals Metathesis access to monocyclic iminocyclitol-based therapeutic agents

2011 ◽  
Vol 7 ◽  
pp. 699-716 ◽  
Author(s):  
Ileana Dragutan ◽  
Valerian Dragutan ◽  
Carmen Mitan ◽  
Hermanus CM Vosloo ◽  
Lionel Delaude ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Metabolic Disorders ◽  
Therapeutic Agents ◽  
Comparative Performance ◽  
Common Diseases ◽  
Metathesis Reactions ◽  
Recent Developments ◽  
Metathesis Catalysts ◽  
Steric Control

By focusing on recent developments on natural and non-natural azasugars (iminocyclitols), this review bolsters the case for the role of olefin metathesis reactions (RCM, CM) as key transformations in the multistep syntheses of pyrrolidine-, piperidine- and azepane-based iminocyclitols, as important therapeutic agents against a range of common diseases and as tools for studying metabolic disorders. Considerable improvements brought about by introduction of one or more metathesis steps are outlined, with emphasis on the exquisite steric control and atom-economical outcome of the overall process. The comparative performance of several established metathesis catalysts is also highlighted.

scholarly journals Olefin metathesis in nano-sized systems

2011 ◽  
Vol 7 ◽  
pp. 94-103 ◽  
Author(s):  
Didier Astruc ◽  
Abdou K Diallo ◽  
Sylvain Gatard ◽  
Liyuan Liang ◽  
Cátia Ornelas ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Covalent Attachment ◽  
Enyne Metathesis ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
Nano Catalysts

The interplay between olefin metathesis and dendrimers and other nano systems is addressed in this mini review mostly based on the authors’ own contributions over the last decade. Two subjects are presented and discussed: (i) The catalysis of olefin metathesis by dendritic nano-catalysts via either covalent attachment (ROMP) or, more usefully, dendrimer encapsulation – ring closing metathesis (RCM), cross metathesis (CM), enyne metathesis reactions (EYM) – for reactions in water without a co-solvent and (ii) construction and functionalization of dendrimers by CM reactions.

scholarly journals Ruthenium indenylidene “1st generation” olefin metathesis catalysts containing triisopropyl phosphite

2015 ◽  
Vol 11 ◽  
pp. 1520-1527 ◽  
Author(s):  
Stefano Guidone ◽  
Fady Nahra ◽  
Alexandra M Z Slawin ◽  
Catherine S J Cazin
Keyword(s):  
Experimental Data ◽  
Thermal Stability ◽  
Olefin Metathesis ◽  
Synergistic Effects ◽  
Metathesis Reactions ◽  
Metathesis Catalysts ◽  
Ru Species

The reaction of triisopropyl phosphite with phosphine-based indenylidene pre-catalysts affords “1st generation” cis-complexes. These have been used in olefin metathesis reactions. The cis-Ru species exhibit noticeable differences with the trans-Ru parent complexes in terms of structure, thermal stability and reactivity. Experimental data underline the importance of synergistic effects between phosphites and L-type ligands.

Synthesis and characterization of non-chelating ruthenium–indenylidene olefin metathesis catalysts derived from substituted 1,1-diphenyl-2-propyn-1-ols

2015 ◽  
Vol 39 (3) ◽  
pp. 1858-1867 ◽  
Author(s):  
Baoyi Yu ◽  
Yu Xie ◽  
Fatma B. Hamad ◽  
Karen Leus ◽  
Alex A. Lyapkov ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
First Generation ◽  
Catalytic Performance ◽  
Ruthenium Catalysts ◽  
Synthesis And Characterization ◽  
Metathesis Reactions ◽  
Metathesis Catalysts

The synthesis and characterization of four first-generation modified non-chelating indenylidene ruthenium catalysts is reported, as well as their catalytic performance in olefin metathesis reactions.

scholarly journals The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2282 ◽  
Author(s):  
Michał Pieczykolan ◽  
Justyna Czaban-Jóźwiak ◽  
Maura Malinska ◽  
Krzysztof Woźniak ◽  
Reto Dorta ◽  
...  
Keyword(s):  
High Activity ◽  
Olefin Metathesis ◽  
Double Bonds ◽  
Carbene Ligands ◽  
Grubbs Catalyst ◽  
Metathesis Reactions ◽  
Metathesis Catalysts

A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified N-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing standard SIMes and SIPr ligands (4a and 4b) gave the best results in metathesis of substrates with more accessible C–C double bonds. At the same time, catalysts bearing engineered naphthyl-substituted NHC ligands (4d–e) exhibited high activity towards formation of tetrasubstituted C–C double bonds, the reaction which was traditionally Achilles’ heel of the nitro-activated Hoveyda–Grubbs catalyst.

scholarly journals Halide exchanged Hoveyda-type complexes in olefin metathesis

2010 ◽  
Vol 6 ◽  
pp. 1091-1098 ◽  
Author(s):  
Julia Wappel ◽  
César A Urbina-Blanco ◽  
Mudassar Abbas ◽  
Jörg H Albering ◽  
Robert Saf ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Ring Opening ◽  
Catalytic Performance ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
Metathesis Catalysts

The aims of this contribution are to present a straightforward synthesis of 2nd generation Hoveyda-type olefin metathesis catalysts bearing bromo and iodo ligands, and to disclose the subtle influence of the different anionic co-ligands on the catalytic performance of the complexes in ring opening metathesis polymerisation, ring closing metathesis, enyne cycloisomerisation and cross metathesis reactions.

ChemInform Abstract: Phosphabicyclononane-Containing Ru Complexes: Efficient Pre-Catalysts for Olefin Metathesis Reactions.

ChemInform ◽  
2008 ◽  
Vol 39 (20) ◽  
Author(s):  
Fabien Boeda ◽  
Herve Clavier ◽  
Margaritha Jordaan ◽  
Wolfgang H. Meyer ◽  
Steven P. Nolan
Keyword(s):  
Olefin Metathesis ◽  
Metathesis Reactions ◽  
Ru Complexes
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