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Concept

Réaction de Grignard

Publications associées (29)

Recent progress in alkynylation with hypervalent iodine reagents

Jérôme Waser, Eliott Hugo Joran Le Du

Although alkynes are one of the smallest functional groups, they are among the most versatile building blocks for organic chemistry, with applications ranging from biochemistry to material sciences. Alkynylation reactions have traditionally relied on the u ...

Royal Society of Chemistry2023

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

Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

Jérôme Waser, Stephanie Grace Elizabeth Amos

Ethynylbenziodoxolones (EBXs) have recently emerged as potent reagents for the alkynylation of radicals. Their combination with photocatalysis allows the synthesis of valuable alkynes at room temperature. Herein, we discuss two photomediated strategies for ...

2022

Development of C-C and C-O bond cleavage catalysts for the depolymerization of plastics

Wei-Tse Lee

Chemical recycling of plastics provides more flexibility for materials circulation than landfill disposal or incineration. Intensive research efforts have been devoted to maximizing the efficiency of chemical recycling through catalyst development. The fro ...

EPFL2022

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Jérôme Waser, Eliott Hugo Joran Le Du, Julien Aymeric Borrel

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most f ...

2022

Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

Jérôme Waser, Julien Aymeric Borrel

Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach e ...

2021

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Jérôme Waser, Franck Le Vaillant, Stephanie Grace Elizabeth Amos, Diana Cavalli

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alle ...

Wiley-VCH Verlag GmbH2021

Operando XANES from first-principles and its application to iridium oxide

Nicola Marzari, Francesco Nattino

Efficient electro-catalytic water-splitting technologies require suitable catalysts for the oxygen evolution reaction (OER). The development of novel catalysts could benefit from the achievement of a complete understanding of the reaction mechanism on irid ...

ROYAL SOC CHEMISTRY2020

Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

Jérôme Waser, Stefano Nicolai, Stephanie Grace Elizabeth Amos

We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolu ...

2020

Role of OH Intermediates during the Au Oxide Electro-Reduction at Low pH Elucidated by Electrochemical Surface-Enhanced Raman Spectroscopy and Implicit Solvent Density Functional Theory

Nicola Marzari, Francesco Nattino

Molecular understanding of the electrochemical oxidation of metals and the electro-reduction of metal oxides is of pivotal importance for the rational design of catalyst-based devices where metal(oxide) electrodes play a crucial role. Operando monitoring a ...

AMER CHEMICAL SOC2020

Direct Observation of Aggregation-Induced Emission Mechanism

Anne-Clémence Corminboeuf, Antonio Prlj, Kun-Han Lin

The mechanism of aggregation-induced emission, which overcomes the common aggregation-caused quenching problem in organic optoelectronics, is revealed by monitoring the real time structural evolution and dynamics of electronic excited state with frequency ...

Wiley-VCH Verlag GmbH2020

Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Kay Severin, Abdusalom Suleymanov

Aromatic compounds containing triazenyl groups (N3RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has change ...

Wiley-VCH Verlag GmbH2021

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

Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds

Jérôme Waser, Franck Le Vaillant

The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensivel ...

2019

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2

Martin Hulla

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

EPFL2019

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Lionel Schouwey

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first syn ...

2019

Activity-Based Screening of Homogeneous Catalysts through the Rapid Assessment of Theoretically Derived Turnover Frequencies

Anne-Clémence Corminboeuf, Matthew Wodrich, Boodsarin Sawatlon

In homogeneous catalysis, the turnover frequency (TOF) and turnover number (TON) are the most commonly used quantities that experimentally describe catalytic activity. Computational studies, on the other hand, generally yield the ubiquitous free energy pro ...

AMER CHEMICAL SOC2019

Photoredox-Catalyzed Decarboxylation for the Transfer of Alkynes and Nitriles Using Hypervalent Iodine Reagents

Franck Le Vaillant

Aliphatic alkynes and nitriles are privileged motifs in organic chemistry. Therefore, alkynes and nitriles have played a central role for the exploration and development of novel strategies to forge C-C bonds in efficient manner. They are broadly used as v ...

EPFL2019

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

CO2 hydrogenation reaction over pristine Fe, Co, Ni, Cu and Al2O3 supported Ru: Comparison and determination of the activation energies

Andreas Züttel, Wen Luo, Noris André Gallandat, Robin Tobias Andreas Mutschler, Emanuele Moioli

Fe, Co, Ni and Cu are the main non-noble industrially significant catalysts in the CO2 and CO gas phase hydrogenation reaction towards hydrocarbons and alcohols. These catalysts are typically supported on metal oxides such as SiO2, TiO2, Al2O3 and ZnO, in ...

ACADEMIC PRESS INC ELSEVIER SCIENCE2018