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Jérôme Waser

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Publications associées (186)

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Tyrosine bioconjugation with hypervalent iodine

Jérôme Waser, Natalia Gasilova, Laure Menin, Nina Declas

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 ...

2022

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

Jérôme Waser, Matthew Wodrich, Franck Le Vaillant

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 ...

2017

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

Jérôme Waser, Fides Benfatti, Florian Patrick Marie Daniel De la Barre De Nanteuil

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 ...

2012

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

Jérôme Waser, Christian Heinis, Xinjian Ji, Xingyu Liu

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 ...

Wiley-VCH Verlag GmbH2023

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

Jieping Zhu, Jérôme Waser, Qian Wang, Pierre Gérard Joseph Palamini, Raphaël Michel Henri Simonet-Davin

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 ...

2024

C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation

Jérôme Waser, Franck Le Vaillant, Marion Marie-Agnès Garreau

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. ...

Wiley-VCH Verlag GmbH2019

Activation of aminocyclopropanes via radical intermediates

Jérôme Waser, Mingming Wang

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 ...

Royal Society of Chemistry2022

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

Jérôme Waser, Guillaume Dominique Pisella, Nieves Pilar Ramirez Hernandez

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 ...

2021

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

Jérôme Waser, Yifan Li, Durga Prasada Rao Hari, Maria Victoria Vita

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 ...

Wiley-Blackwell2016

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

Jérôme Waser, Guillaume Dominique Pisella, Alec Gagnebin

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 ...

2020

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

Jérôme Waser, Romain Gaëtan Tessier, Javier De Ceballos Cerrajeria, Raj Kumar Nandi

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 ...

Wiley-VCH Verlag GmbH2020

Inhibition of Thiol‐Mediated Uptake with Irreversible Covalent Inhibitors

Jérôme Waser, Eliott Hugo Joran Le Du, Elija Grinhagena, Abhaya Kumar Mishra

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 ...

Wiley-VHCA AG2021

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

Jérôme Waser, Jonathan Brand, Davinia Fernández González

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 ...

2010

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

Jérôme Waser, Stefano Nicolai

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 ...

Royal Soc Chemistry2024

Direct Alkynylation of Indole and Pyrrole Heterocycles

Jérôme Waser, Jonathan Brand

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 ...

Wiley-VCH Verlag GmbH2009

Photocatalytic Redox Reactions for In-Source Peptide Fragmentation

Hubert Girault, Jérôme Waser, Liang Qiao, Hongyan Bi

In-source photocatalytic redox reactions based on a photosensitive target plate have been developed to realize peptide fragmentation during laser desorption ionization. Sample peptides and glucose are simply deposited on a spot of sintered TiO2 nanoparticl ...

2009

Umpolung Of Electron-Rich Heteroarenes With Hypervalent Iodine Reagents

Jérôme Waser, Raj Kumar Nandi

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 ...

PERGAMON-ELSEVIER SCIENCE LTD2021

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

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

Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction

Jérôme Waser, Filippo De Simone

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 ...

2009