Publications associées à Composé carbonylé α,β-insaturé

New Applications of 1,3,2-Diazaphospholenes in Catalysis

The constant urge to construct new molecules in an economical and sustainable fashion led to the development of numerous metal-catalyzed transformations. Organocatalysts consisting of abundant and more sustainable elements offer an elegant solution to over ...

EPFL2024

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

Formation of carbonyl compounds during ozonation of lake water and wastewater: Development of a non-target screening method and quantification of target compounds

Urs von Gunten, Joanna Maria Houska

Ozonation of natural waters is typically associated with the formation of carbonyl compounds (aldehydes, ketones and ketoacids), a main class of organic disinfection byproducts (DBPs). However, the detection of carbonyl compounds in water and wastewater is ...

PERGAMON-ELSEVIER SCIENCE LTD2023

Chlorination of amides: Kinetics and mechanisms of formation of N-chloramides and their reactions with phenolic compounds

Urs von Gunten, Tianqi Zhang

Amides are common constituents in natural organic matter and synthetic chemicals. In this study, we investi-gated kinetics and mechanisms of the reactions of chlorine with seven amides, including acetamide, N-meth-ylformamide, N-methylacetamide, benzamide, ...

2023

Mechanistic insights on interactions of dissolved organic matter with chemical oxidants: quantification of reactive sites and identification of oxidation byproducts

Joanna Maria Houska

Chemical oxidants including ozone (O3), chlorine (HOCl/OCl-) and chlorine dioxide (ClO2) are applied for disinfection of drinking water. To cope with water scarcity and the increased risks associated with the presence of micropollutants, water treatment sy ...

EPFL2023

Organocatalytic Enantioselective Diels-Alder Reaction of 2-Trifluoroacetamido-1,3-dienes with alpha,beta-Unsaturated Ketones

Qian Wang, Jieping Zhu, Xinqi Zhu

We report herein the first examples of chiral phosphoric acid-catalyzed enantioselective Diels-Alder reactions between 2-trifluoroacetamido-1,3-dienes 1 and alpha,beta-unsaturated carbonyl compounds 2. Polysubstituted 1-acetamido cyclohexenes 3 were formed ...

Wiley-VCH Verlag GmbH2023

Migrative Carbofluorination of Saturated Amides Enabled by Pd-Based Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Anne-Clémence Corminboeuf, Hua Wu, Simone Gallarati, Guoqiang Yang

Directly editing an all-carbon quaternary carbon itself of nonstrained acyclic molecules remains underexploited despite the recent advances in the fields of both C–H and C–C bond activation. Herein, we report a palladium-catalyzed migrative carbofluorinati ...

ACS2022

Catalytic enantioselective Pictet-Spengler reaction of carbonyl compounds: Development and application to the asymmetric total synthesis of indole alkaloids

Rémi Julien Sylvain Andres

This thesis consists in an extensive study about the enantioselective Pictet-Spengler reaction (EPSR) and its application to the total synthesis of monoterpene indole alkaloids (MIAs). The general introduction presents the literature background about this ...

EPFL2022

Reactions of alpha,beta-Unsaturated Carbonyls with Free Chlorine, Free Bromine, and Combined Chlorine

Urs von Gunten

Chemical disinfectants employed in water and wastewater treatment can produce a variety of transformation products, including carbonyl compounds (e.g., saturated and unsaturated aldehydes and ketones). Experiments conducted under conditions relevant to chl ...

AMER CHEMICAL SOC2021

Developing the Catalytic Applications of 1,3,2-Diazaphospholenes

John Henry Reed

The development of new catalytic methods for organic synthesis is a critical endeavour in order to obviate the economic and ecological drawbacks of stoichiometric organic synthesis. While catalysis can offer significant advantages in terms of atom-economy, ...

EPFL2021

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

Multilevel screening of computation-ready, experimental metal-organic frameworks for natural gas purification

Berend Smit, Zhi Li, Yi Zhang

In this study, traditional Monte Carlo simulation and density functional theory-based structural optimization methods were combined to screen computation-ready experimental metal-organic framework (MOF) database for the application of natural gas purificat ...

WILEY2021

An Oculus to Profile and Probe Target Engagement In Vivo: How T-REX Was Born and Its Evolution into G-REX

Yimon Aye, Chloé Rogg

Here we provide a personal account of innovation and design principles underpinning a method to interrogate precision electrophile signaling that has come to be known as "REX technologies". This Account is framed in the context of trying to improve methods ...

AMER CHEMICAL SOC2021

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

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Qian Wang, Jieping Zhu, Dylan Jean Robert Dagoneau

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

WILEY-V C H VERLAG GMBH2020

1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids

Nicolai Cramer, John Henry Reed

The potent nucleophilicity and remarkably low basicity of 1,3,2- diazaphospholenes (DAPs) is exploited in a catalytic, metal-free 1,4-reduction of free ,-unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the car ...

Wiley-VCH Verlag2020

Catalytic Enantioselective Transformations with Chiral Cyclopentadienyl Ruthenium(II) Complexes

Sung Hwan Park

The chemistry of cyclopentadienyl ruthenium(II) complexes plays an important role in ruthenium catalysis because of its high potential for various transformations. However, asymmetric catalysis with chiral cyclopentadienyl ruthenium(II) complexes is still ...

EPFL2020

Nature of Synergy between Bronsted and Lewis Acid Sites in Sn-Beta Zeolites for Polyoxymethylene Dimethyl Ethers Synthesis

Oliver Kröcher, Alimohammad Bahmanpour, Christophe Jean Baranowski

The role of Lewis and Bronsted acid sites and their potential synergy remains ambiguous for the production of polyoxymethylene dimethyl ethers (OME), which are suitable as a Diesel substitute. Here, this synergistic effect was investigated by using a serie ...

WILEY-V C H VERLAG GMBH2019

Asymmetric Alkenyl C−H Functionalization by Cp x Rh III forms 2 H ‐Pyrrol‐2‐ones through [4+1]‐Annulation of Acryl Amides and Allenes

Nicolai Cramer, Shouguo Wang, Yang Liu

An efficient CpxRhIII‐catalyzed enantioselective alkenyl C−H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β‐unsaturated‐γ‐lactams bearing a qua ...

Wiley-VCH Verlag GmbH2019

Ozonation of Para-Substituted Phenolic Compounds Yields p-Benzoquinones, Other Cyclic α,β-Unsaturated Ketones, and Substituted Catechols

Urs von Gunten, Peter Rudolf Tentscher

Phenolic moieties are common functional groups in organic micropollutants and in dissolved organic matter, and are exposed to ozone during drinking water and wastewater ozonation. Although unsubstituted phenol is known to yield potentially genotoxic p-benz ...

2018