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Concept

Halogénoalcane

Publications associées (27)

Editing Tetrasubstituted Carbon: Dual C–O Bond Functionalization of Tertiary Alcohols Enabled by Palladium-Based Dyotropic Rearrangement

Jieping Zhu, Qian Wang, Baochao Yang, Tristan Corentin Pierre Delcaillau

Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent ...

2024

Diverting the 5-exo-Trig Oxypalladation to Formally 6-endo-Trig Fluorocycloetherification Product through 1,2-O/Pd(IV) Dyotropic Rearrangement

Jieping Zhu, Qian Wang, Jing Gong, Jing Gong

Pd-catalyzed cyclizative functionalization of γ-hydroxyalkenes affords tetrahydrofuran derivatives via a key 5-exo-trig oxypalladation step. Herein, we report a palladium(II)-catalyzed, Selectfluor-mediated formal 6-endo-trig fluorocycloetherification of γ ...

2023

Modelling the coupled mercury-halogen-ozone cycle in the central Arctic during spring

Julia Schmale, Ivo Fabio Beck, Hélène Paule Angot

Near-surface mercury and ozone depletion events occur in the lowest part of the atmosphere during Arctic spring. Mercury depletion is the first step in a process that transforms long-lived elemental mercury to more reactive forms within the Arctic that are ...

2023

Synthetic Receptors with Micromolar Affinity for Chloride in Water

Kay Severin, Farzaneh Fadaei Tirani, Cesare Berton, Sylvain Alexandre Marie Sudan, Damien Wen Chen

A water-soluble coordination cage was obtained by reaction of Pd(NO3)2 with a 1,3-di(pyridin-3-yl)benzene ligand featuring a short PEG chain. The cavity of the metal-organic cage contains one nitrate anion, which is readily replaced by chloride. The appare ...

Wiley-VCH Verlag GmbH2023

Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Kay Severin, Nicolai Cramer, Carl Thomas Bormann, Jin Fay Tan

The 1,1,2,2-tetrafluoroethylene unit is prevalent in bioactive molecules and functional materials. Despite being in principle a straightforward strategy to access this motif, the direct tetrafluorination of alkynes involves very hazardous or inconvenient r ...

2022

Substantial contribution of iodine to Arctic ozone destruction

Julia Schmale, Ivo Fabio Beck, Hélène Paule Angot, Lubna Dada

Unlike bromine, the effect of iodine chemistry on the Arctic surface ozone budget is poorly constrained. We present ship-based measurements of halogen oxides in the high Arctic boundary layer from the sunlit period of March to October 2020 and show that io ...

2022

Anionic character of the conduction band of sodium chloride

Klaus Kern, Abhishek Grewal

The alkali halides are ionic compounds. Each alkali atom donates an electron to a halogen atom, leading to ions with full shells. The valence band is mainly located on halogen atoms, while, in a traditional picture, the conduction band is mainly located on ...

Nature Portfolio2022

High Aspect Ratio Au Microflakes via Gap-Assisted Synthesis

Giulia Tagliabue, Fateme Kiani Shahvandi

Ultrathin and extra-large single-crystalline Au microflakes (Au MFs) have a huge potential in applications ranging from nanophotonics to catalysis. Yet, wet chemical synthesis approaches cannot access this size range due to the proportionality between grow ...

2022

Apparent 6-endo-trig Carbofluorination of Alkenes Enabled by Palladium-Based Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Jing Gong

Alkene difunctionalization featuring an intramolecular carbometallation step has been developed into a powerful transformation in organic synthesis. The 5-exo-trig carbometallation is in general highly favored over the alternative 6-endo-trig cyclization. ...

Wiley-VCH Verlag GmbH2022

Renewable monomer and polymer thereof

Jeremy Luterbacher, Stefania Bertella, Lorenz Perry Manker, Graham Reid Dick

Described is a compound having the structure (I), (II) or (V), Formulae(I), (II), (V), wherein R1 is -H, -CH2OH or -CH(OH)CH2OH; R2 is -H, -OH, or -CH2OH; R3 is -H, -OH, or -CH2OH; n is 0 or 1; p is 0 or 1; R10 is hydrogen or a hydrocarbon moiety with 1 to ...

2021

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Xile Hu, Srikrishna Bera, Deyun Qian

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation metho ...

AMER CHEMICAL SOC2021

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Xile Hu, Runze Mao, Xiangli Yi, Lara Lavrencic

Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carbox ...

Wiley-VCH Verlag GmbH2021

Antiproliferative Activities of Diimine-Based Mixed Ligand Copper(II) Complexes

Rosario Scopelliti

A series of Cu(diimine)(X-sal)(NO3) complexes, where the diimine is either 2,2'-bipyridine (bpy) or 1,10-phenanthroline (phen) and X-sal is a monoanionic halogenated salicylaldehyde (X = Cl, Br, I, or H), have been synthesized and characterized by elementa ...

AMER CHEMICAL SOC2020

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

Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals

Guido Barzanò

C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...

EPFL2020

Reactions of nitrogen-containing compounds with ozone: kinetics and mechanisms

Sung Eun Lim

Nitrogen-containing moieties are widespread in natural waters in dissolved organic nitrogen and micropollu-tants. They are often susceptible to an electrophilic attack of ozone because of the electron-rich nature of the neutral form of nitrogen in organic ...

EPFL2020

Enantioselective C(sp(3))-C(sp(3)) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis

Xile Hu, Runze Mao, Srikrishna Bera

Cross-coupling of two alkyl fragments is an efficient method to produce organic molecules rich in sp(3)-hybridized carbon centres, which are attractive candidate compounds in drug discovery. Enantioselective C(sp(3))-C(sp(3)) coupling is challenging, espec ...

2020

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the gamma or delta po ...

Wiley-VCH Verlag GmbH2020

Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition

Xile Hu, Guido Barzanò, Alexis Baptiste Cheseaux

Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stere ...

2019

Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C-H Functionalizations

Nicolai Cramer, Yun-Suk Jang, Kristers Ozols

The synthesis of a set of cobalt(III)-complexes equipped with trisubstituted chiral cyclopentadienyl ligands is reported, and their steric and electronic parameters are mapped. The application potential of these complexes for asymmetric C-H functionalizati ...

2019