Papers by Cédric Fischmeister
Advanced Synthesis & Catalysis
The silver-catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nan... more The silver-catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields.
Comptes Rendus Chimie
Membrane modification Supported catalysis OSN in toluene a b s t r a c t This study is aimed at d... more Membrane modification Supported catalysis OSN in toluene a b s t r a c t This study is aimed at developing an innovative concept for the preparation of an olefin metathesis catalytic membrane. This goal was achieved by grafting a Grubbs II precatalyst on a zirconia membrane generating a tailor-made HoveydaeGrubbs precatalyst on the surface of an ultrafiltration inorganic membrane. The obtained membranes were characterized by different techniques evidencing the grafting. The catalytic activity was also evaluated in a model ring-closing metathesis reaction. According to our knowledge, this manuscript reports the first ever so sophisticated catalytic membrane based on an organometallic complex of ruthenium. The proof of concept was achieved, although the membrane grafting must be improved for better catalytic activity.
ChemSusChem
The catalytic reductive amination of levulinic acid (LA) into pyrrolidones with an iridium cataly... more The catalytic reductive amination of levulinic acid (LA) into pyrrolidones with an iridium catalyst using H2 as hydrogen source is reported. The chemoselective iridium catalyst displayed high efficiency for the synthesis of a variety of N-substituted 5-methyl-2pyrrolidones and N-arylisoindolinones. N-Substituted 5-methyl-2pyrrolidone was evaluated as a bio-sourced substitute solvent to NMP (N-Methyl-pyrrolidone) in the catalytic arylation of 2phenylpyridine.
Twisted polymers, uses thereof and processes for the preparation of statistical copolymers
Electropolymerization of pi-Conjugated Oligomers Containing Phosphole Cores and Terminal Thienyl Moieties: Optical and Electronic Properties We thank the CNRS, the MENRT, the Conseil Régional de Bretagne for financial support of this work and Prof. C. Moinet for helpful discussions
Angewandte Chemie International Edition
Olefin Metathesis in Green Organic Solvents and without Solvent
Theory and Practice, 2014
Ruthenium catalyzed ethenolysis of renewable oleonitrile
European Journal of Lipid Science and Technology, 2014
ABSTRACT Oleonitrile is a bio-sourced compound readily obtained by ammoniation of the renewable o... more ABSTRACT Oleonitrile is a bio-sourced compound readily obtained by ammoniation of the renewable oleic acid. The production of the short chain undecenitrile by ethenolysis (cross-metathesis with ethylene) of oleonitrile is reported. Optimization of the reaction conditions led to promising TONs of 1400 with high selectivity for the ethenolysis products. From a series of catalysts tested, the bulky and activated M71 SiPr catalyst enabled the best performances. The influence of feed purification method was investigated in details and it was found that thermal treatment of the feed was required to ensure the highest productivity.Practical applicationsThe selective ethenolysis of oleonitrile provides a direct access to bio-sourced 9-decenitrile and 1-decene. These two compounds of interest for the synthesis of polymers precursors have also some potential use as fuel additives.
Catalytic Alkene Metathesis in Ionic Liquids
NATO Science Series II: Mathematics, Physics and Chemistry, 2007
Page 1. CATALYTIC ALKENE METATHESIS IN IONIC LIQUIDS CEDRIC FISCHMEISTER ... Campus de Beaulieu 3... more Page 1. CATALYTIC ALKENE METATHESIS IN IONIC LIQUIDS CEDRIC FISCHMEISTER ... Campus de Beaulieu 35042 Rennes, France. E-mail: cedric.fischmeister @univ-rennes1.fr Phone: + 33 2 23 23 59 98. Fax: + 33 2 23 23 69 39 ...
Cross-metathesis of fatty acid methyl esters with acrolein: An entry to a variety of bifunctional compounds
European Journal of Lipid Science and Technology, 2014
ABSTRACT The cross-metathesis of renewable fatty acid methyl esters with acrolein was investigate... more ABSTRACT The cross-metathesis of renewable fatty acid methyl esters with acrolein was investigated. The bifunctional formyl-esters obtained are interesting compounds for further transformations into bifunctional polymer precursors. Several experimental parameters and ruthenium catalysts have been evaluated. Best results were obtained with thermally pre-treated fatty acid methyl esters (FAMEs). The reactions performed with high efficiency with low catalyst loadings allowing TONs as high at 1000. An acetal protected acrolein was also used, enabling improvement of the reaction performances. A tandem cross-metathesis/hydrogenation reaction without isolation of the formyl intermediate delivered the expected alcohol ester in good yield.Practical applications: The cross-metathesis of FAMEs with acrolein provides access to a broad range of bifunctional compounds of interest for the manufacture of polymers, considering the multiple post-transformations of the formyl group availableThe ruthenium-catalyzed cross-metathesis of fatty acid methyl esters with acrolein is presented. The bifunctional formyl-esters are valuable precursors for subsequent transformations such as the tandem cross-metathesis/hydrogenation reaction delivering a hydroxyl-ester in one step.
Nucleophilic Additions to Alkynes and Reactions via Vinylidene Intermediates
MURAHASHI:RUTHENIUM O-BK, 2004
ABSTRACT For Abstract see ChemInform Abstract in Full Text.
ChemInform Abstract: C-H Bond Functionalization in Water Catalyzed by Carboxylato Ruthenium(II) Systems
ChemInform, 2010
ABSTRACT The presented cross-coupling reaction strongly depends on the nature of both substrates ... more ABSTRACT The presented cross-coupling reaction strongly depends on the nature of both substrates and proceeds without formation of any metal-salt waste.
ChemInform, 2012
The first examples of an oxidative alkenylation of N-arylpyrazoles by cooperative action of a Ru(... more The first examples of an oxidative alkenylation of N-arylpyrazoles by cooperative action of a Ru(III) catalyst and acetate ligands in air are described. -(AROCKIAM, P. B.; FISCHMEISTER, C.; BRUNEAU*, C.; DIXNEUF, P. H.; Green Chem. 13 (2011) 11, 3075-3078, http://dx.doi.org/10.1039/c1gc15875a ; Inst. Sci. Chim., CNRS, Univ. Rennes, F-35042 Rennes, Fr.; Eng.) -R. Staver 13-141
Z selectivity: Recent advances in one of the current major challenges of olefin metathesis
ABSTRACT The stereoselective formation of carbon–carbon double bonds is a longstanding topic in o... more ABSTRACT The stereoselective formation of carbon–carbon double bonds is a longstanding topic in organic chemistry. Since the early 90s, catalytic olefin metathesis has emerged as a synthetic tool of choice for the creation of carbon–carbon double bonds, and its use is now widespread. However, except for the synthesis of small cycles, the reversible character of olefin metathesis usually results in the formation of the thermodynamic E product, and more generally in mixtures of E and Z products. This issue has been addressed in different ways; these are reviewed herein. Synthetic protocols, which aim at the selective synthesis of Z olefins, for example, sequential alkyne metathesis/cis-hydrogenation, and the use of removable silyl groups, are summarized. Tailor-made molybdenum, tungsten and ruthenium catalysts, which allow for very high stereoselectivity, are also reviewed. The advances achieved with these methods and catalysts are illustrated by the synthesis of various natural products or their precursors.
Terminal conjugated dienes via a ruthenium-catalyzed cross-metathesis/elimination sequence: application to renewable resources
Catalysis Science & Technology, 2014
Two-step synthesis of terminal 1,3-dienes catalyzed by two different ruthenium complexes.
RSC Advances, 2012
The ruthenium-catalyzed cross-metathesis of eugenol derivatives with electron deficient olefins i... more The ruthenium-catalyzed cross-metathesis of eugenol derivatives with electron deficient olefins is reported. It is shown that in the presence of ruthenium catalysts, eugenol and its O-protected derivatives have a high tendency to undergo carbon-carbon double bond migration before and after metathesis leading to the formation of conjugated styrene derivatives. The addition of 1,4benzoquinone suppresses these isomerization reactions and provides an efficient access to new polyfunctional phenol derivatives upon cross-metathesis of the biosourced eugenol with acrylates, acrylonitrile and acrylamides. Cite this: RSC Advances, 2012, 2, 9584-9589 www.rsc.org/advances PAPER 9584 | RSC Adv., 2012, 2, 9584-9589
Catalysis Communications, 2014
Homogeneous catalysis is a major actor of modern chemistry with a growing impact on clean and sus... more Homogeneous catalysis is a major actor of modern chemistry with a growing impact on clean and sustainable chemical processes. However, for many industrial applications of homogeneously catalyzed reactions, an easy separation and recovery of the catalyst should be guaranteed. Temperature-dependent multicomponent solvent systems (TMS) have been evaluated in ruthenium catalyzed olefin metathesis transformations. Propylene carbonate was found a suitable solvent for the ruthenium catalyzed ring-closing and cross-metathesis transformations of a variety of substrates including renewable fatty esters. The potential of a TMS system consisting of propylene carbonate/ethyl acetate/cyclohexane was then evaluated in the cross-metathesis of the renewable methyl 10-undecenoate with methyl acrylate and acrylonitrile.
The Journal of Physical Chemistry B, 2004
Electrochemiluminescence (ECL) experiments were carried out in acetonitrile electrolytes with pla... more Electrochemiluminescence (ECL) experiments were carried out in acetonitrile electrolytes with platinum electrodes coated with poly(2,3-dibutoxy-1,4-phenylenevinylene), DB-PPV. By application of alternating anodic and cathodic potential steps, positive and negative polarons were produced in the polymer. The annihilation reaction resulted in ECL transients. Model calculations were conducted for analyzing the electron and ion transport processes in the deposit as well as the kinetics of the annihilation reaction. Very good agreement with the experiments was found when the charging of the interfacial double layer was taken into account. The annihilation reaction was concluded to proceed under diffusion control. The emission spectrum was found to have its maximum at 480 nm. This is a shift by -10 nm with respect to the fluorescence spectrum of DB-PPV in chloroform, and by -40 nm with respect to the electroluminescence spectrum observed from the solid-state. The ECL emission spectrum did not depend on the sequence in which the positive and negative polarons were formed, in agreement with the expectation for an ECL mechanism.
Highly efficient and economic synthesis of new substituted amino-bispyridyl derivatives via copper and palladium catalysis
Tetrahedron Letters, 2008
... 2 R. van Asselt, E. Rijnberg and CJ Elsevier. Organometallics, 13 (1994), p. 706. 3 PK Byers,... more ... 2 R. van Asselt, E. Rijnberg and CJ Elsevier. Organometallics, 13 (1994), p. 706. 3 PK Byers, AJ Canty, BW Skelton and AH White. J. Chem. Soc., Chem. ... 5 AJ Canty. Acc. Chem. Res., 25 (1992), p. 83. 6 DG Brown, PK Byers and AJ Canty. Organometallics, 9 (1990), p. 1231. 7. ...
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Papers by Cédric Fischmeister