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Concept

Rendement chimique

Publications associées (31)

Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction

Jieping Zhu, Qian Wang, Chenxu Liu, Qiang Feng

We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in go ...

Wiley-VCH Verlag GmbH2024

Dual Photoredox and Copper Catalysis: Enantioselective 1,2-Amidocyanation of 1,3-Dienes

Jieping Zhu, Qian Wang, Weisi Guo, Dan Forster

Dual photoredox−transition-metal catalysis has emerged as a powerful tool for the development of chemical transformations. However, its application in the selective difunctionalization of 1,3-dienes remains essentially unexploited. By the synergistic actio ...

2023

Nanomole-scale photochemical thiol-ene chemistry for high-throughput late-stage diversification of peptide macrocycles

Alexander Lund Nielsen, Mischa Schüttel

The photochemical thiol-ene reaction is an efficient method for rapid and chemoselective formation of thioether linkages under mild conditions. It has found widespread use in small-molecule synthesis as well as peptide and protein chemistry. While high-thr ...

WILEY2023

Charge-Selectively Permeable Self-Healing Microcapsules

Esther Amstad, Chuen-Ru Li

Microcapsules possessing a selective permeability are well-suited vessels for conducting cell studies or chemical reactions that require selective exchanges of reagents over a prolonged time. Most currently reported microcapsules are single-use delivery ca ...

WILEY2023

Synthetic chemistry with nitrous oxide and triazenes

Iris Roswitha Landman

Nitrous oxide (N2O) has gained much interest because of its physiological effects ("laughing gas") and its negative environmental impact ("greenhouse gas", "ozone-depleting substance"): It has a lifetime of more than 100 years in the atmosphere. Its persis ...

EPFL2022

(4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Jérôme Waser, Stefano Nicolai

Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) ...

Wiley-VCH Verlag GmbH2022

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

Diiron Complexes with a Bridging Functionalized Allylidene Ligand: Synthesis, Structural Aspects, and Cytotoxicity

Paul Joseph Dyson, Lucinda Kate Batchelor

Regio- and stereoselective nucleophilic attack of cyanide (from NBu4CN) to cationic diiron vinyliminium compounds [Fe2Cp2(CO)(mu-CO){mu-eta(1):eta(3)-C-(R')C(R '')-CNMe2}]CF3SO3 ([1a-f]CF3SO3) affords the nitrile-aminoallylidene derivatives 2a-f in good to ...

AMER CHEMICAL SOC2020

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

Catalytic valorization of the acetate fraction of biomass to aromatics and its integration into the carboxylate platform

Jeremy Luterbacher, Benjamin Pierre Le Monnier, Masoud Talebi Amiri, Ydna Marie Questell-Santiago, Jher Hau Yeap, Bartosz Rozmyslowicz

In many plant species, the acetate fraction is the fourth most prominent fraction by weight after cellulose, hemicellulose and lignin, and can be easily extracted as a single stable molecule, acetic acid, at high yields. Despite this, upgrading the acetate ...

2019

Optimization of Lignin Extraction from Pine Wood for Fast Pyrolysis by Using γ-valerolactone-Based Binary Solvent System

Jeremy Luterbacher

Fast pyrolysis of lignin is a promising method to produce aromatic chemicals and fuels. Lignin structure and pyrolysis conditions determine the liquid yield and product selectivity. Extraction of pine wood using γ-valerolactone (GVL) mixed with water in th ...

2019

Mechanochemistry-assisted hydrolysis of softwood over stable sulfonated carbon catalysts in a semi-batch process

Oliver Kröcher, Frédéric Vogel, David Ferdinand Scholz

The hydrolysis of lignocellulose is the first step in saccharide based bio-refining. The recovery of homogeneous acid catalysts imposes great challenges to the feasibility of conventional hydrolysis processes. Herein, we report a strategy to overcome these ...

2019

Synthesis of bicyclo[3.1.0]hexanes by (3+2) annulation of cyclopropenes with aminocyclopropanes

Jérôme Waser, Bastian Antoine Rodolphe Claude Muriel, Alec Gagnebin

We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yie ...

2019

Production and characterization of stabilized lignin

Masoud Talebi Amiri

Lignocellulosic biomass is a sustainable source of renewable carbon, and it is the most abundant form of terrestrial biomass. The three main constituents of lignocellulosic biomass are cellulose, hemicellulose, and lignin. The monomers from these biopolyme ...

EPFL2019

Magnetic properties of on-surface synthesized single-ion molecular magnets

Harald Brune, Stefano Rusponi, Marina Pivetta, Jan Gui-Hyon Dreiser, Christian Wäckerlin, Aparajita Singha, Katharina Johanna Diller

We perform on-surface synthesis of single-ion molecular magnets on an Ag(111) surface and characterize their morphology, chemistry, and magnetism. The first molecule we synthesize is TbPc2 to enable comparison with chemically synthesized and subsequently s ...

2019

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Pivotal Role of the Basic Character of Organic and Salt Catalysts in C-N Bond Forming Reactions of Amines with CO2

Paul Joseph Dyson, Martin Hulla

Organocatalysts promote a range of C-N bond forming reactions of amines with CO2. Herein, we review these reactions and attempt to identify the unifying features of the catalysts that allows them to promote a multitude of seemingly unrelated reactions. Ana ...

Wiley-VCH Verlag GmbH2020

Indole Alkaloids, Macrocycles and Heterocycles : Interplay between Methodological Development and Total Synthesis

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

Contributions to the Chemistry of N2O and 1-Alkynyltriazenes

Loïc Nicolas Jeanbourquin

This thesis describes the utilization of nitrous oxide N2O as an oxidant in oxidative cou-pling reactions and as a nitrogen atom donor in the synthesis of 1-alkynyltriazene and further reactivity of the latter. An overview of N2O and its reactivity is give ...

EPFL2018