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Concept

Élimination réductrice

Publications associées (27)

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

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

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023

Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Jieping Zhu, Anne-Clémence Corminboeuf, Qian Wang, Simone Gallarati, Takuji Fujii

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds

Ashis Kumar Das

Transition metal-catalyzed C-H activation is a powerful tool for the synthesis of organic building blocks, materials, and natural products. Over the last decade, directing-group-assisted metal-catalyzed C-H functionalization has attracted increasing intere ...

EPFL2022

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

Atropo‐Enantioselective Oxidation‐Enabled Iridium(III)‐Catalyzed C−H Arylations with Aryl Boronic Esters

Nicolai Cramer, Lukasz Piotr Wozniak

Atropo-enantioselective biaryl coupling through C−H bond functionalization is an emerging technology allowing direct construction of axially chiral molecules. This approach is largely limited to electrophilic coupling partners. We report a highly atropo-en ...

Wiley-VCH Verlag GmbH2021

The Genesis of Molecular Volcano Plots

Anne-Clémence Corminboeuf, Matthew Wodrich, Boodsarin Sawatlon, Michael Markus Busch

For the past two decades, linear free energy scaling relationships and volcano plots have seen frequent use as computational tools that aid in understanding and predicting the catalytic behavior of heterogeneous and electrocatalysts. Based on Sabatier's pr ...

American Chemical Society2021

Iron-Catalyzed Reductive Coupling of Alkyl Iodides with Alkynes To Yield cis-Olefins: Mechanistic Insights from Computation

Xile Hu

In a recent study, a new procedure for Z-selective olefin synthesis by reductive coupling of alkyl iodides with terminal alkynes in the presence of iron salts is described. This transformation is representative of many newly developed synthetic routes thro ...

AMER CHEMICAL SOC2020

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal ca ...

Wiley-VCH Verlag GmbH2019

Discovery of a Highly Active Catalyst for Hydrogenolysis of C-O Bonds via Systematic, Multi-metallic Catalyst Screening

Paul Joseph Dyson, Ning Yan, Antoine Philippe Van Muyden, Sviatlana Siankevich

Hydrogenolysis of C-O bonds is a highly challenging reaction with the most efficient catalysts based on bimetallic assemblies. Systematic studies to identify the optimum metal combination have not been performed and, therefore, we designed a method to scre ...

Wiley-VCH Verlag2019

Nickamine and Analogous Nickel Pincer Catalysts for Cross-Coupling of Alkyl Halides and Hydrosilylation of Alkenes

Xile Hu, Zhikun Zhang, Renyi Shi

CONSPECTUS: Ligand development plays an essential role in the advance of homogeneous catalysis. Tridentate, meridionally coordinating ligands, commonly termed pincer ligands, have been established as a privileged class of ligands in catalysis because they ...

American Chemical Society2019

Unexpected Indirect Dynamics in Base-Induced Elimination

Eduardo Carrascosa Casado

Base-induced elimination (E2) and bimolecular nucleophilic substitution (S(N)2) are two of the most versatile reactions that are important in preparative organic chemistry. These stereospecific reactions are often found in direct competition with each othe ...

AMER CHEMICAL SOC2019

Decarboxylative C(sp3)–N cross-coupling via synergetic photoredox and copper catalysis

Xile Hu, Runze Mao

Amines are a quintessential moiety in bioactive molecules, pharmaceuticals and organic materials. Transition-metal-catalysed C–N coupling of aryl electrophiles has been established as a powerful and reliable method for amine synthesis. However, the analogo ...

2018

Exploring the Limitation of Molecular Water Oxidation Catalysts

Anne-Clémence Corminboeuf, Alberto Fabrizio, Michael Markus Busch

Linear free energy scaling relationships (LFESRs) and volcano plots are routinely used to assess the performance of heterogeneous electrocatalysts and have only recently been concretely exploited in homogeneous catalysis. These tools efficiently compare an ...

AMER CHEMICAL SOC2018

Improving the Thermodynamic Profiles of Potential Suzuki-Miyaura Cross-Coupling Catalysts by Altering the Electrophilic Coupling Component

Anne-Clémence Corminboeuf, Matthew Wodrich

As a heavily used technique for forming new C-C bonds, developing new catalysts and reaction conditions for Suzuki-Miyaura cross-coupling reactions is desirable. Here, using volcano plots, the influence of the electrophilic coupling component in catalytic ...

Wiley-VCH Verlag2018

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

Jieping Zhu, Qian Wang, 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

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Fedor Zhurkin

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017

Synthesis of Diversely Functionalized Oxindoles Enabled by Migratory Insertion of Isocyanide to a Transient σ-Alkylpalladium(II) Complex

Jieping Zhu, Qian Wang, Wangqing Kong

Palladium-catalyzed intramolecular carbopalladation of N-aryl acrylamides followed by migratory insertion of an isocyanide-coordinated C(sp3)-Pd intermediate afforded an alkylimidoyl-Pd(II) complex, which can be intercepted by a nucleophile, including hete ...

Wiley-Blackwell2016

Lanthanide(II) Complexes Supported by N,O-Donor Tripodal Ligands: Synthesis, Structure, and Ligand-Dependent Redox Behavior

Rosario Scopelliti, Marinella Mazzanti, Julie Renée Michelle Andrez

The preparation and characterization of a series of complexes of the Yb and Eu cations in the oxidation state II and III with the tetradentate N,O-donor tripodal ligands (tris(2-pyridylmethyl)amine (TPA), BPA(-) (HBPA=bis(2-pyridylmethyl)(2-hydroxybenzyl)a ...

2015