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Jérôme Waser

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Related publications (186)

Page 3 of 10

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

Jérôme Waser, Tobias Michael Milzarek

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 ...

Wiley-VCH Verlag GmbH2023

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

Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

Jérôme Waser, Phillip Gulliver Dominic Greenwood, Erwann Stefan Grenet

1,2-Amino alcohols and -aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is pe ...

2019

Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines

Jérôme Waser, Filippo De Simone

Activated cyclopropanes, such as vinyl and carbonyl cyclopropanes, are useful building blocks in organic chemistry due to their exceptional reactivity. This review focuses on the use of cyclopropyl carbonyls and imines in cyclization and cycloaddition reac ...

Georg Thieme Verlag2009

Synthesis of Bicyclo[1.1.1]pentane Z‐Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents

Najung Lee, Jonas Dechent, Jérôme Waser, Elija Grinhagena

Bicyclo[1.1.1]pentanes (BCPs) are well‐studied bioisosteres for para‐substituted benzene rings and numerous methods for synthesizing 1,3‐difunctionalized BCPs have been developed. However, synthetic approaches to access vinyl BCP motifs remain limited, wit ...

Wiley2025

Palladium-Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification

Jérôme Waser, Ugo Jonathan Orcel

Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and ...

Wiley-Blackwell2015

Catalytic (3+2) annulation of donor-acceptor aminocyclopropane monoesters and indoles

Jérôme Waser, Emma Gabrielle Louise Robert, Vincent Géry C Pirenne

The efficient catalytic activation of donor-acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into c ...

2021

Interrupted Polonovski Strategy for the Synthesis of Functionalized Amino Acids and Peptides

Jérôme Waser, Emmanuelle Madeline Dominique Allouche, Christine Alice Jacqueline Marty

The alpha-functionalization of carbamate-protected hydroxylamine glycine derivatives, acting as imine surrogates via an interrupted Polonovski reaction, is described to access functionalized amino acid derivatives. The addition of C, N, O, and S nucleophil ...

2024

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

Cost-informed Bayesian reaction optimization †

Jérôme Waser, Anne-Clémence Corminboeuf, Rubén Laplaza Solanas, Alexandre Alain Schöpfer, Jan Weinreich

Bayesian optimization (BO) is an efficient method for solving complex optimization problems, including those in chemical research, where it is gaining significant popularity. Although effective in guiding experimental design, BO does not account for experi ...

Royal Society of Chemistry (RSC)2024

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

Thomas Rossolini, Jérôme Waser, Stefano Nicolai, Ashis Kumar Das

A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturate ...

2022

Asymmetric Organocatalysis Meets Hypervalent Iodine Chemistry for the alpha-Functionalization of Carbonyl Compounds

Jérôme Waser, Fides Benfatti, Davinia Fernández González

Wiley-VCH Verlag2012

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

Platinum-Catalyzed Domino Reactionwith Benziodoxole Reagents for Accessing Benzene-Alkynylated Indoles

Jérôme Waser, Yifan Li

Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrro ...

Wiley-Blackwell2015

Cyclic Hypervalent Iodine Reagents and Iron Catalysts: The Winning Team for Late-Stage C-H Azidation

Jérôme Waser, Maria Victoria Vita

1+1=3: by combining the exceptional properties of benziodoxolone reagents and iron catalysts, Sharma and Hartwig have achieved an important breakthrough for the late-stage C-Hazidation of complex molecules. Nevertheless, moderate yields and selectivities w ...

Wiley-Blackwell2015

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Jérôme Waser, Stefano Nicolai, Franck Le Vaillant, Stephanie Grace Elizabeth Amos, Alec Gagnebin

Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxo ...

2019

Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents

Jérôme Waser, Christian Heinis, Elija Grinhagena, Gontran Sangouard, Javier De Ceballos Cerrajeria

Easy access to a wide range of structurally diverse stapled peptides is crucial for the development of inhibitors of protein-protein interactions. Herein, we report bis-functional hypervalent iodine reagents for two-component cysteine-cysteine and cysteine ...

Wiley-VCH Verlag GmbH2021

Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents

Chao Wang, Jérôme Waser, Reto Frei, Durga Prasada Rao Hari

In this study, we present a highly efficient method for proteomic profiling of cysteine residues in complex proteomes and in living cells. Our method is based on alkynylation of cysteines in complex proteomes using a clickable alkynyl benziodoxolone bearin ...

Wiley-Blackwell2015

Nucleoside Analogues: Synthesis from Strained Rings

Jérôme Waser, Jérémy Vuilleumier, Sophie Lucie Racine

Nucleoside analogues are widely employed as bioactive compounds against cancer and viral infections. Consequently, it is important to develop efficient synthetic methods to access them with high efficiency and structural diversity. Herein, we present a ful ...

Wiley-V C H Verlag Gmbh2016

Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light-Mediated Selective CÀ C Cleavage Strategy

Duncan Keith Brownsey, Jérôme Waser, Matthew Wodrich, Vu Trung Tin Nguyen

We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading to selective cleavage of the more substituted carbon-carbon bond. Depending on the substrate structure, extended alkenes were isol ...

Wiley2024