Publications associées à Organopalladium chemistry

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

Qian Wang, Jieping Zhu, Qiang Feng, Chenxu Liu

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

Palladium-based supramolecular assemblies: from complex structures to water-soluble anion-receptors

Sylvain Alexandre Marie Sudan

The combination of palladium salts and bipyridyl ligands can lead to the formation of a large variety of coordination complexes, with different shapes and sizes, displaying a very versatile host-guest chemistry. Increasing their structural complexity remai ...

EPFL2024

Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction

Jérôme Waser, Mikus Purins, Lucas Antoine Théo Eichenberger

Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-se ...

Royal Society of Chemistry2023

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

Qian Wang, Jieping Zhu, 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

Assessing the effect of O2 dithering on CH4 oxidation on Pd/Al2O3

Oliver Kröcher, Davide Ferri

Under periodic lean/rich operation generated by repeated O2 pulses (O2-dithering), the abatement of CH4 and NO is enhanced compared to static operation. However, it is not well understood how the dithering parameters (pulse amplitude and frequency) affect ...

ELSEVIER SCIENCE SA2023

Development of metal-organic frameworks based on N-heterocyclic ligands

Ilia Kochetygov

Metal-organic frameworks (MOFs) have firmly established in the field of porous materials since their early discovery in the 1990s. With a plethora of applications, these materials offer endless possibilities owing to their tunable, modular nature. The vast ...

EPFL2022

Catalytic Enantioselective Synthesis of Morpholinones Enabled by Aza-Benzilic Ester Rearrangement

Qian Wang, Jieping Zhu, Hua Wu, Yuping He

Chiral morpholinone is an important building block in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective methods for the construction of this N,O-heterocycle remain scarce. We report herein a chiral phosphoric ...

2021

Reduction of PdO/Al2O3 in Liquid Cyclohexane Followed In Situ by ATR-IR, High-Energy XRD, and XAS

Oliver Kröcher, Davide Ferri, Thibault Xavier Florian Fovanna

Supported Pd-based catalysts used in heterogeneously catalyzed liquid phase processes often undergo an activation step through reduction of the oxide phase or of the oxidic passivation layer prior to reaction. An oxidized Pd/Al2O3 catalyst was reduced by u ...

AMER CHEMICAL SOC2021

Copper-Catalyzed Oxyvinylation of Diazo Compounds

Jérôme Waser, Guillaume Dominique Pisella, Alec Gagnebin

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was su ...

2020

Synthesis and characterization of iron-clathrochelates and their applications in materials science

José Luis Bila

This thesis focuses on the design and the synthesis of mono- and dinuclear iron clathrochelate complexes and their applications in materials science. Dinuclear iron clathrochelate complexes can be synthesized in different oxidation states: i. as negative ...

EPFL2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Daria Grosheva

Asymmetric metal-catalyzed C-H functionalization has enjoyed great success as a powerful strategy for the rapid construction of elaborate structures from simple precursors. For example, aryl (pseudo)halides have been extensively employed as electrophilic s ...

EPFL2019

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Jérôme Waser, Matthew Wodrich, Paola Caramenti, Romain Gaëtan Tessier, Nina Declas

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

Pd Nanoparticles Stabilized by Hypercrosslinked Polystyrene Catalyze Selective Triple C-C Bond Hydrogenation and Suzuki Cross-Coupling

Lioubov Kiwi

This paper describes the synthesis of Pd-containing catalysts based on nonfunctionalized hypercrosslinked polystyrene via impregnation with Pd acetate. Developed Pd nanoparticulate catalyst allowed achieving conversion of aryl halide up to 90% in Suzuki cr ...

2019

From isonitrile to nitrile via ketenimine intermediate: Palladium-catalyzed 1,1-carbocyanation of ally carbonate by alpha-isocyanoacetate

Qian Wang, Jieping Zhu, Guanyinsheng Qiu, Charlotte Marie Sornay, Sheng-Cai Zheng, David Savary

A palladium-catalyzed 1,1-carbocyanation of allyl carbonate by alpha-quaternary alpha-isocyanoacetate was developed. Formation of ketenimine followed by homolysis of the C-N bond and recombination of the resulting caged radical pair was proposed to account ...

PERGAMON-ELSEVIER SCIENCE LTD2018

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions

Qian Wang, Jieping Zhu, Wangqing Kong

Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3)-Pd intermediate using diboron–water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectiviti ...

Wiley-Blackwell2017

Highly dispersed cobalt oxides nanoparticles on activated carbon fibres as efficient structured catalysts for the transfer hydrogenation of m-nitrostyrene

Paul Joseph Dyson, Lioubov Kiwi, Oliver Anthony Beswick, Alexander Parastaev

The facile preparation of structured catalysts featuring highly-dispersed non-precious metal (Fe, Ni, Co) oxide nanoparticles stabilized within a super-microporous network of activated carbon fibres (ACF) is described. The catalyst morphology was controlle ...

Elsevier Science Bv2017

Synthesis of Alkynylated Heterocycles by Direct C-H Alkynylation or Domino Alkynylation Reactions

Yifan Li

Heterocycles are important compounds in organic chemistry. To introduce functional groups on heterocycles or synthesize functionalized heterocycles stays a hot topic of research. Among all the functional groups, alkynes attracted a lot of attention not onl ...

EPFL2016

Pd-Nanoparticles Confined Within Hollow Polymeric Framework as Effective Catalysts for the Synthesis of Fine Chemicals

Lioubov Kiwi

Encapsulation of metal nanoclusters in porous solid polymer materials is a promising approach to combine the outstanding properties of both, heterogeneous and homogeneous catalysts. We report heterogeneous nano-engineered catalysts containing Pd-nanopartic ...

Springer/Plenum Publishers2016

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Qian Wang, Jieping Zhu, Shuo Tong, Zhengren Xu, Mathias Mamboury

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles via a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxyl and amino groups we ...

Wiley-Blackwell2015