Cross metathesis of methyl oleate (MO) with terminal, internal olefins by ruthenium catalysts: factors affecting the efficient MO conversion and the selectivity

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 100925-100930 ◽  
Author(s):  
Nor Wahida Awang ◽  
Ken Tsutsumi ◽  
Barbora Huštáková ◽  
Siti Fairus M. Yusoff ◽  
Kotohiro Nomura ◽  
...  
Keyword(s):  
Methyl Oleate ◽  
High Selectivity ◽  
Ruthenium Catalysts ◽  
Factors Affecting ◽  
Cross Metathesis

Cross metathesis (CM) of methyl oleate (MO) with cis-4-octene, cis-stilbene, allyltrimethylsilane by RuCl2(PCy3)(IMesH2)(CHPh) yielded CM products with high MO conversion, high selectivity; the effect of olefin substituents, conditions was explored.

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.

Synthesis of Conjugated Triynes via Alkyne Metathesis

2019 ◽  
Author(s):  
Idriss Curbet ◽  
Sophie Colombel-Rouen ◽  
Romane Manguin ◽  
Anthony Clermont ◽  
Alexandre Quelhas ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
High Selectivity ◽  
Alkyne Metathesis ◽  
Cross Metathesis ◽  
Synthetic Strategy ◽  
Sterically Hindered ◽  
Site Selective

<div> <div> <div> <div> <p>The synthesis of conjugated triynes by molybdenum-catalyzed alkyne metathesis is reported. Strategic to the success of this approach is the utilization of sterically-hindered diynes that allowed for the site- selective alkyne metathesis to produce the desired con- jugated triyne products. The steric hindrance of alkyne moiety was found to be crucial in preventing the for- mation of diyne byproducts. This novel synthetic strategy was amenable to self- and cross-metathesis providing straightforward access to the corresponding symmetrical and dissymmetrical triynes with high selectivity. </p> </div> </div> </div> </div>

scholarly journals Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

Data in Brief ◽  
2018 ◽  
Vol 20 ◽  
pp. 190-195
Author(s):  
Pablo D. Nieres ◽  
Andrés F. Trasarti ◽  
Carlos R. Apesteguía
Keyword(s):  
Methyl Oleate ◽  
Cross Metathesis ◽  
Equilibrium Data ◽  
The Cross

Tandem Catalytic Acrylonitrile Cross-Metathesis and Hydrogenation of Nitriles with Ruthenium Catalysts: Direct Access to Linear α,ω-Aminoesters from Renewables

ChemSusChem ◽  
2012 ◽  
Vol 5 (8) ◽  
pp. 1410-1414 ◽  
Author(s):  
Xiaowei Miao ◽  
Cédric Fischmeister ◽  
Christian Bruneau ◽  
Pierre H. Dixneuf ◽  
Jean-Luc Dubois ◽  
...  
Keyword(s):  
Ruthenium Catalysts ◽  
Direct Access ◽  
Cross Metathesis ◽  
Hydrogenation Of Nitriles

scholarly journals 3-Substituted 1-Naphthamidomethyl-C-galactosyls Interact with Two Unique Sub-Sites for High-Affinity and High-Selectivity Inhibition of Galectin-3

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4554 ◽  
Author(s):  
Alexander Dahlqvist ◽  
Santanu Mandal ◽  
Kristoffer Peterson ◽  
Maria Håkansson ◽  
Derek T. Logan ◽  
...  
Keyword(s):  
High Selectivity ◽  
Structural Elements ◽  
High Affinity ◽  
Cross Metathesis ◽  
Terminal Domain ◽  
Naphthoic Acid ◽  
Galectin 3 ◽  
Inflammatory Processes ◽  
Further Development ◽  
Substituted 1

The galectins are a family of galactose-binding proteins playing key roles in inflammatory processes and cancer. However, they are structurally very closely related, and discovery of highly selective inhibitors is challenging. In this work, we report the design of novel inhibitors binding to a subsite unique to galectin-3, which confers both high selectivity and affinity towards galectin-3. Olefin cross metathesis between allyl β-C-galactopyranosyl and 1-vinylnaphthalenes or acylation of aminomethyl β-C-galactopyranosyl with 1-naphthoic acid derivatives gave C-galactopyranosyls carrying 1-naphthamide structural elements that interacted favorably with a galectin-3 unique subsite according to molecular modeling and X-ray structural analysis of two inhibitor-galectin-3 complexes. Affinities were down to sub-µM and selectivities over galectin-1, 2, 4 N-terminal domain, 4 C-terminal domain, 7, 8 N-terminal domain, 9 N-terminal domain, and 9 C-terminal domain were high. These results show that high affinity and selectivity for a single galectin can be achieved by targeting unique subsites, which holds promise for further development of small and selective galectin inhibitors.

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.

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