Terminal conjugated dienes via a ruthenium-catalyzed cross-metathesis/elimination sequence: application to renewable resources

2014 ◽  
Vol 4 (7) ◽  
pp. 2064-2071 ◽  
Author(s):  
Hallouma Bilel ◽  
Naceur Hamdi ◽  
Fethi Zagrouba ◽  
Cédric Fischmeister ◽  
Christian Bruneau
Keyword(s):  
Renewable Resources ◽  
Ruthenium Complexes ◽  
Conjugated Dienes ◽  
Cross Metathesis

Two-step synthesis of terminal 1,3-dienes catalyzed by two different ruthenium complexes.

scholarly journals Modification of Polyhedral Oligomeric Silsesquioxanes (POSS) Molecules by Ruthenium Catalyzed Cross Metathesis

Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1722 ◽  
Author(s):  
Justyna Czaban-Jóźwiak ◽  
Łukasz Woźniak ◽  
Artur Ulikowski ◽  
Katarzyna Kwiecińska ◽  
Adam Rajkiewicz ◽  
...  
Keyword(s):  
Ruthenium Complexes ◽  
Polyhedral Oligomeric Silsesquioxanes ◽  
Ru Catalyst ◽  
Cross Metathesis

The scope of ruthenium (Ru)-catalyzed cross metathesis (CM) of allyl-decorated polyhedral oligomeric silsesquioxanes (POSS) was explored. A variety of different commercial and non-commercial ruthenium complexes were tested to determine that the nitro-activated Ru catalyst is optimal for this transformation. The reported transformation was used to prepare selected hybrid steroid-POSS compounds.

scholarly journals NHC Ligand Effects on Ru-Catalyzed Cross-Metathesis of Renewable Materials

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 904
Author(s):  
Veronica Paradiso ◽  
Raffaele Contino ◽  
Fabia Grisi
Keyword(s):  
Renewable Resources ◽  
Olefin Metathesis ◽  
Ethyl Oleate ◽  
Building Blocks ◽  
Metathesis Reaction ◽  
Renewable Materials ◽  
Ligand Effects ◽  
Cross Metathesis ◽  
Chemical Manufacturing ◽  
Catalytic Performances

As petrochemical resources become increasingly scarce and expensive, much attention has been focused on renewable resources from biomass as alternative options for producing basic building blocks for chemical manufacturing. Catalytic olefin metathesis represents a powerful tool to transform biosourced structural motifs in valuable commodity, fine, and specialty chemicals. In that respect, the appropriate choice of the catalyst is the key issue of each metathesis transformation. The current study examines the influence of different N-heterocyclic carbene (NHC) ligands containing one or two N-alkyl substituents on the efficiency of Hoveyda–Grubbs-type catalysts in the cross-metathesis reaction of ethyl oleate with cis-1,4-diacetoxy-2-butene and cross-metathesis of eugenol acetate with cis-1,4-dichloro-2-butene. Interestingly, the introduction of alkyl N-substituents in the NHC ligand was revealed as beneficial for catalytic performances in the examined cross-metathesis (CM) reactions, leading to higher activity and/or selectivity than those observed in the presence of the classical, commercially available Hoveyda–Grubbs second generation catalyst (HGII).

scholarly journals Chemoselective Construction of Substituted Conjugated Dienes Using an Olefin Cross-Metathesis Protocol.

ChemInform ◽  
2005 ◽  
Vol 36 (21) ◽  
Author(s):  
Timothy W. Funk ◽  
Jon Efskind ◽  
Robert H. Grubbs
Keyword(s):  
Conjugated Dienes ◽  
Cross Metathesis

scholarly journals Cyclic Alkyl Amino Ruthenium Complexes—Efficient Catalysts for Macrocyclization and Acrylonitrile Cross Metathesis

ACS Catalysis ◽  
2017 ◽  
Vol 7 (8) ◽  
pp. 5443-5449 ◽  
Author(s):  
Rafał Gawin ◽  
Andrzej Tracz ◽  
Michał Chwalba ◽  
Anna Kozakiewicz ◽  
Bartosz Trzaskowski ◽  
...  
Keyword(s):  
Ruthenium Complexes ◽  
Cross Metathesis

Functionalization vs. degradation of 1,4-polybutadiene by ruthenium complex catalyzed reaction with vinylsilanes

2001 ◽  
Vol 79 (5-6) ◽  
pp. 775-779 ◽  
Author(s):  
Bogdan Marciniec ◽  
Ewa Malecka ◽  
Jacek Gulinski ◽  
Monika Grundwald-Wyspianska ◽  
Mariusz Lewandowski
Keyword(s):  
Ruthenium Complex ◽  
Ruthenium Complexes ◽  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Higher Temperature ◽  
Partial Degradation

Polybutadiene (I) containing 91% of 1,4-(cis-trans) units and 9% of 1,2-units in the presence of vinyltriethoxysilane (II) and ruthenium catalysts RuCl2(PPh3)3 (III), RuHCl(CO)(PPh3)3 (IV), and [RuCl2(CO)3]2 (V) at 100-130°C undergoes functionalization and (or) partial degradation as an effect of competitive silylative coupling of =C-H and cross-metathesis of I with II. Significant degradation of I occurs at lower temperatures (100-110°C) (particularly when the process is carried out in air), but exclusive functionalization of I is observed at higher temperature (120-130°C) regardless of the atmosphere (air or argon) used.Key words: functionalization, degradation, polybutadiene, ruthenium complexes.

Cross-metathesis of vinyltriethoxysilane with olefins catalyzed by ruthenium complexes

1991 ◽  
Vol 65 (1-2) ◽  
pp. 113-125 ◽  
Author(s):  
Zenon Foltynowicz ◽  
Bogdan Marciniec ◽  
Cezary Pietraszuk
Keyword(s):  
Ruthenium Complexes ◽  
Cross Metathesis

scholarly journals The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups

2011 ◽  
Vol 7 ◽  
pp. 1-8 ◽  
Author(s):  
Arno Behr ◽  
Jessica Pérez Gomes
Keyword(s):  
Methyl Oleate ◽  
Renewable Resources ◽  
Value Added ◽  
Ruthenium Catalysts ◽  
Protecting Groups ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Functional Monomers ◽  
Cross Metathesis ◽  
The Cross

Background: α,ω-Difunctional substrates are useful intermediates for polymer synthesis. An attractive, sustainable and selective (but as yet unused) method in the chemical industry is the oleochemical cross-metathesis with preferably symmetric functionalised substrates. The current study explores the cross-metathesis of methyl oleate (1) with cis-2-butene-1,4-diyl diacetate (2) starting from renewable resources and quite inexpensive base chemicals. Results: This cross-metathesis reaction was carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. The influence of protecting groups present in the substrates on the necessary catalyst loading was also investigated. Conclusions: The value-added methyl 11-acetoxyundec-9-enoate (3) and undec-2-enyl acetate (4) are accessed with nearly quantitative oleochemical conversions and high cross-metathesis selectivity under mild reaction conditions. These two cross-metathesis products can be potentially used as functional monomers for diverse sustainable polymers.

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