Publications de Jérôme Waser

Chattez avec Graph Search

Posez n’importe quelle question sur les cours, conférences, exercices, recherches, actualités, etc. de l’EPFL ou essayez les exemples de questions ci-dessous.

AVERTISSEMENT : Le chatbot Graph n'est pas programmé pour fournir des réponses explicites ou catégoriques à vos questions. Il transforme plutôt vos questions en demandes API qui sont distribuées aux différents services informatiques officiellement administrés par l'EPFL. Son but est uniquement de collecter et de recommander des références pertinentes à des contenus que vous pouvez explorer pour vous aider à répondre à vos questions.

Hypervalent iodine reagents have recently emerged as powerful tools for late-stage peptide and protein functionalization. Herein we report a tyrosine bioconjugation methodology for the introduction of hypervalent iodine onto biomolecules under physiologica ...

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and no ...

The first enantiospecific [3+2] annulation of D-A amino-cyclopropanes with ketones is reported herein (see scheme; Phth = phthaloyl). The reaction is catalyzed by 5 mol % of tin(IV) chloride at -78 °C and gives aminotetra-hydrofurans bearing a C5-quaternar ...

Herein, we report a novel strategy for the modification of peptides based on the introduction of highly reactive hypervalent iodine reagents-ethynylbenziodoxolones (EBXs)-onto peptides. These peptide-EBXs can be readily accessed, by both solution- and soli ...

The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp(3))-H bond functionalization protocols have been developed relying on this elementary step. We report herein copper- and iron-cata ...

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. ...

Aminocyclopropanes are versatile building blocks for accessing high value-added nitrogen-containing products. To control ring-opening promoted by ring strain, the Lewis acid activation of donor-acceptor substituted systems is now well established. Over the ...

Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their ...

Multicomponent reactions provide efficient means to access molecular complexity. Herein, we report a copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers. Exten ...

Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on ...

The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by a simple Cu(I) salt is described. This three-component reaction allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor ani ...

Thiol-mediated uptake is emerging as method of choice to penetrate cells. This study focuses on irreversible covalent inhibitors of thiol-mediated uptake. High-content high-throughput screening of the so far largest collection of hypervalent iodine reagent ...

Hot alkyne! The in situ generation of Ethynyl-1,2-BenziodoXol-3(1H)-one (EBX) from the corresponding silyl protected reagent using TBAF is reported. EBX displayed exceptional acetylene transfer ability to stabilized enolates, even at –78 °C. The mild react ...

Bicyclic carbocycles containing a high fraction of Csp3 have become highly attractive synthetic targets because of the multiple applications they have found in medicinal chemistry. The formal cycloaddition of bicyclobutanes (BCBs) with two- or three-atom p ...

Easy does it: The unique properties of benziodoxolone alkynyl periodinane 1 and gold catalysts have allowed the development of a high yielding, operationally simple (room temperature, no dry solvents or inert conditions, commercially available catalyst) re ...

Five-membered heterocycles are well known for their innate nucleophilicity. In contrast, reaction of these heterocycles as electrophiles is less established and has become only recently an intensively investigated research area in synthetic chemistry. The ...

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 ...

Ring strain confers to the cyclopropane ring an exceptional reactivity. Nevertheless, activation of the cyclopropane ring is usually needed to allow ring-opening reactions under mild conditions. The introduction of one or several carbonyl functionalities o ...

The first trifluoromethylation of vinylbenziodoxolones (VBX) is reported herein. The synthetic method is based on the use of bench-stable, high-valent copper(III) species, and the reaction can be initiated under thermal conditions and/or irradiation (365 n ...

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 ...

Jérôme Waser

Chattez avec Graph Search

Tyrosine bioconjugation with hypervalent iodine

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones

Peptide-Hypervalent Iodine Reagent Chimeras: Enabling Peptide Functionalization and Macrocyclization

Benzylic C(sp3)-H Azidation: Copper vs Iron Catalysis

C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation

Activation of aminocyclopropanes via radical intermediates

Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation

Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers

Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells

Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines

Inhibition of Thiol‐Mediated Uptake with Irreversible Covalent Inhibitors

Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters

Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes

Direct Alkynylation of Indole and Pyrrole Heterocycles

Umpolung Of Electron-Rich Heteroarenes With Hypervalent Iodine Reagents

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

Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction

Synthesis of Trifluoromethylated Alkenes: Hypervalent Iodine Meets High-Valent Copper

Copper-Catalyzed Oxyvinylation of Diazo Compounds