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Concept

Époxyde

Publications associées (23)

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Rémi Hugo Lavernhe

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Asymmetric (CpRh)-Rh-x(III)-Catalyzed Acrylic Acid C-H Functionalization with Allenes Provides Chiral gamma-Lactones

Nicolai Cramer, Shouguo Wang

A chiral cyclopentadienyl (Cp-x) ligand featuring the semi-saturated H8-binaphthyl backbone as the chiral element was developed. Its application potential was demonstrated by (CpRhIII)-Rh-x-catalyzed C-H bond functionalization of acryl acids and allenes, e ...

AMER CHEMICAL SOC2020

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Jérôme Waser, Bastian Antoine Rodolphe Claude Muriel, Vincent Géry C Pirenne

This review describes the development of enantioselective methods for the ring opening of cyclopropanes. Both approaches based on the reaction of nonchiral cyclopropanes and (dynamic) kinetic resolutions and asymmetric transformations of chiral substrates ...

2021

Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

Jérôme Waser, Stefano Nicolai, Stephanie Grace Elizabeth Amos

We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolu ...

2020

Copper(I) Based Photoredox Chemistry

Murat Alkan

Photoredox catalysis has become a powerful tool for chemists. However, the reliance on expensive Ir and Ru based photoredox catalysts (PC) motivates research for more sustainable options. Copper complexes based on favorable photophysical properties, high a ...

EPFL2020

Copper-Catalyzed Oxyalkynylation of C-S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents

Jérôme Waser, Guillaume Dominique Pisella, Julien Aymeric Borrel

We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most ...

2019

Catalyst support and solvent effects during lignin depolymerization and hydrodeoxygenation

Jeremy Luterbacher, Florent Emmanuel Héroguel

We studied and compared the hydrodeoxygenation (HDO) and depolymerization of aldehyde-stabilized lignin and 4-propylguaiacol (PG), a model lignin monomer. We demonstrated by liquid phase adsorption that PG HDO catalyzed by Ru/C can be achieved in isooctane ...

2019

Intricacies of Cation-Anion Combinations in Imidazolium Salt-Catalyzed Cycloaddition of CO2 Into Epoxides

Paul Joseph Dyson, Gabor Laurenczy, Felix Daniel Bobbink, Martin Hulla, Dmitry Vasilyev, Florent Menoud

The cycloaddition of CO2 into epoxides catalyzed by imidazolium and related salts continues to attract attention due to the industrial importance of the cyclic carbonate products. The mechanism of the imidazolium-catalyzed transformation has been proposed ...

2018

"Palladium-Catalyzed Diamination of Alkynes in Synthesis of Tetracycles" and "Copper-Catalyzed Cyanoalkylation of Unactivated Alkenes"

Minh Tu Ha

The thesis deals with the development of transition metal-catalyzed difunctionalization of alkenes and alkynes, which can be categorized into two major topics: (1) palladium-catalyzed diamination of alkynes for the synthesis of tetracycles; (2) copper-cata ...

EPFL2017

Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors

Rosario Scopelliti

Chiral lactam 2 and three chiral 3-amino alcohols 3-5 have been synthesized and characterized by Sspectroscopic techniques. Regioselective ring opening reaction of chiral styrene oxide by an amine nucle-ophile was confirmed by X-ray diffraction data. Ligan ...

Pergamon-Elsevier Science Ltd2017

Enantioselective Total Synthesis of (−)-Terengganensine A

Jieping Zhu, Qian Wang, Cyril Piemontesi

A seven-step enantioselective total synthesis of (-)-terengganensine A, a complex heptacyclic monoterpene indole alkaloid, was accomplished. Key steps included: a) Noyori's catalytic enantioselective transfer hydrogenation of the iminium salt to set up the ...

Wiley-Blackwell2016

Effects of Grafting Density and Film Thickness on the Adhesion of Staphylococcus epidermidis to Poly(2-hydroxy ethyl methacrylate) and Poly(poly(ethylene glycol)methacrylate) Brushes

Harm-Anton Klok, Sorin Alexandru Ibanescu

Thin polymer films that prevent the adhesion of bacteria are of interest as coatings for the development of infection-resistant biomaterials. This study investigates the influence of grafting density and film thickness on the adhesion of Staphylococcus epi ...

Wiley-Blackwell2016

Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles

Jieping Zhu, Qian Wang, Ala Bunescu

A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation ...

Amer Chemical Soc2015

Copper-Catalyzed Intermolecular Carboetherification of Unactivated Alkenes by Alkyl Nitriles and Alcohols

Jieping Zhu, Qian Wang, Claire Chatalova Sazepin

A three-component carboetherification of unactivated alkenes has been developed allowing the rapid building of complexity from simple starting materials. A wide range of a-substituted styrenes underwent smooth reactions with unactivated alkyl nitriles and ...

Wiley-Blackwell2015

Real Time Determination of the Electronic Structure of Unstable Reaction Intermediates during Au2O3 Reduction

Chemical reactions are always associated with electronic structure changes of the involved chemical species. Determining the electronic configuration of an atom allows probing its chemical state and gives understanding of the reaction pathways. However, of ...

Amer Chemical Soc2014

Fracture Toughness Healing in Epoxy Containing Both Epoxy and Amine Loaded Capsules

Véronique Michaud, Sam Neuser

The feasibility of self-healing epoxy matrices using the same chemistry as the matrix material, namely a standard epoxy-amine system, is demonstrated. The two-component self-healing system is encapsulated in core-shell structures using standard in situ cur ...

Wiley-V C H Verlag Gmbh2014

Cycloaddition of CO2 to epoxides catalyzed by imidazolium-based polymeric ionic liquids

Paul Joseph Dyson, Gabor Laurenczy, Zhaofu Fei, Ning Yan, Felix Daniel Bobbink, Emilia Paunescu, Huizhen Liu

A series of cross-linked ionic polymers based on styrene-functionalized imidazolium salts with chloride, hexafluorophosphate, or tetrafluoroborate counter anions have been prepared and characterized using a range of analytical and spectroscopic techniques ...

Royal Society of Chemistry2013

Atomic Oxygen Chemisorption on Carbon Nanotubes Revisited with Theory and Experiment

Wanda Andreoni, Fabio Pietrucci, Alessandro Curioni

Density-functional-theory based calculations of two single-walled carbon nanotubes of different chirality settle open issues on the sidewall chemisorption of atomic oxygen at low concentrations. Ether groups are the thermodynamically favored configurations ...

Amer Chemical Soc2013

Biphasic Model Describing Soybean Oil Epoxidation with H2O2 in Continuous Reactors

Albert Renken

Epoxidized soybean oil (ESBO) is produced in industry by reacting soybean oil, at 60-70 degrees C, with hydrogen peroxide in the presence of formic or acetic acid. A small amount of sulphuric or phosphoric acid is necessary to catalyze the oxidation of the ...

2012

Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: synthesis from D-mannose

Pierre Vogel

An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxami ...

2010