Personne : Ollevier, Thierry
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Université Laval. Département de chimie
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- PublicationAccès libreHydrogen bond-promoted metal-free hydroamination of alkynes(Thieme, 2019-10-07) Bahri, Janet; Ollevier, Thierry; Tanbouza, Nour; Taillefer, Marc; Monnier, FlorianAn original metal-free regio- and stereoselective intermolecular hydroamination of alkynes is described. Various (E)-enamines were obtained from arylacetylenes and aliphatic secondary amines in the presence of ethylene glycol as a solvent. The latter is assumed to play a major role in the mechanism through hydrogen bonding and proton exchange.
- PublicationAccès libreIron-catalyzed carbene insertion reactions of alpha-diazoesters into Si-H bonds(American Chemical Society, 2017-10-13) Ollevier, Thierry; Keipour, HodaAn efficient iron-catalyzed carbene insertion reaction of α-diazo carbonyl compounds into the Si–H bond was developed. A wide range of α-silylesters was obtained in high yields (up to 99%) from α-diazoesters using a simple iron(II) salt as catalyst.
- PublicationAccès libreBridging lab and industry with flow electrochemistry(Cell Press, 2020-10-22) Ollevier, Thierry; Tanbouza, NourA revitalization of organic electrosynthesis has incited the organic chemistry community to adopt electrochemistry as a green and cost-efficient method for activating small molecules to replace highly toxic and expensive redox chemicals. However, many of the critical challenges of batch electrosynthesis, especially for organic synthesis, still remain. The combination of continuous flow technology and electrochemistry is a potent means to enable industry to implement large scale electrosynthesis. Indeed, flow electrosynthesis helps overcome problems that mainly arise from macro batch electro-organic systems, such as mass transfer, ohmic drop, and selectivity, but this is still far from being a flawless and generic applicable process. As a result, a notable increase in research on methodology and hardware sophistication has emerged, and many hitherto uncharted chemistries have been achieved. To better help the commercialization of wide-scale electrification of organic synthesis, we highlight in this perspective the advances made in large-scale flow electrosynthesis and its future trajectory while pointing out the main challenges and key improvements of current methodologies.
- PublicationAccès libreSynthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air(American Chemical Society, 2019-05-06) Ollevier, Thierry; Li, DazhiA new synthetic method of urea derivatives using copper and air was developed. These mild conditions provided moderate to very good yields for 15 examples (53–93%), while low yields were obtained with sterically hindered substrates (3 examples). The reaction was found to go through an in situ-generated copper-N-heterocyclic carbene, which is then oxidized into cyclic urea derivatives possessing alkyl, benzyl, aryl, hydroxy, Boc-protected, and tertiary amine groups
- PublicationAccès libreIron bis(oxazoline) complexes in asymmetric catalysis(Royal Society of Chemistry, 2015-10-23) Ollevier, ThierryAsymmetric reactions catalyzed by iron complexes have attracted considerable attention because iron is a ubiquitous, inexpensive, and environmentally benign metal. Various chiral iron complexes can be prepared from bis IJ oxazoline) ligands and be used in asymmetric reactions. This overview charts the development and application of chiral iron bis IJ oxazoline) and pyridine-2,6-bis IJ oxazoline) catalysts through their most prominent and innovative uses in asymmetric catalysis, especially in Lewis acid and oxidation catalysis.
- PublicationAccès libreCsF/clinoptilolite : an efficient solid base in SNAr and copper-catalyzed Ullmann reactions(NRC Research Press, 2015-10-19) Keipour, Hoda; Ollevier, Thierry; Hosseini, Abolfaz; Afsari, Amir; Khalilzadeh, Mohammad A.CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.
- PublicationRestreintTransition-metal-free a-arylation of enolizable aryl ketones and mechanistic evidence for a radical process(John Wiley & Sons, Inc., 2015-07-01) Ollevier, Thierry; Fabre, Indira; Pichette Drapeau, Martin; Grimaud, Laurence; Ciofini, Ilaria; Taillefer, MarcThe a-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The a-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.
- PublicationAccès libreNew chiral bis(oxazolinyl) bipyridine ligands and application in the iron catalyzed asymmetric hydrosilylation of ketones(Taras Shevchenko National University of Kyiv., 2015-12-01) Ollevier, Thierry; Levitre, Guillaume; Keipour, Hoda; Jalba, Angela; Lauzon, SamuelC2 symmetrical 6,6'-bis(oxazolinyl)-2,2'-bipyridine (bipybox) chiral ligands have been synthesized from readily available 2,2'-bipyridine. Catalytic asymmetric hydrosilylation of ketones was studied using this family of ligands in the presence of iron(II) acetate.
- PublicationRestreintIron(II)-derived Lewis acid/surfactant combined catalysis for the enantioselective Mukaiyama aldol reaction in pure water(Wiley, 2014-06-26) Lafantaisie, Mathieu; Ollevier, Thierry; Mirabaud, Anaïs; Plancq, BaptisteThe catalytic asymmetric Mukaiyama aldol reaction in pure water was performed by using a combination of iron(II) dodecyl sulfate, a chiral bipyridine ligand, and benzoic acid. By using the obtained iron(II)-derived Lewis acid/surfactant combined catalyst, the desired products were afforded in good yields with high diastereo- and enantioselectivities.
- PublicationAccès libreFeII-catalysed insertion reaction of alpha-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative(Cambridge Royal Society of Chemistry, 2019-10-02) Ollevier, Thierry; Keipour, Hoda; Tanbouza, NourThe insertion reaction of a broad range of diazo compounds into Si–H bonds was found to be efficiently catalysed by Fe(OTf)2 in an emerging green solvent i.e. dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the extrusion of N2 to form an iron carbene intermediate is rate-limiting. The iron-catalysed insertion reaction of methyl α-phenyl-α-diazoacetate into polar X–H bonds (S–H, N–H, and O–H) was also established in DMC.