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Jérôme Waser

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Publications associées (186)

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One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability

Jérôme Waser, Stefano Nicolai, Paola Caramenti, Durga Prasada Rao Hari, Lionel Schouwey, Miyeon Chang

The hypervalent iodine reagent 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step fr ...

2019

Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover

Jérôme Waser, Pierre Gérard Joseph Palamini, Alexandre Alain Schöpfer

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, ...

Wiley2025

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

Wiley-VCH Verlag GmbH2022

Azido-alkynylation of alkenes through radical-polar crossover

Jérôme Waser, Julien Aymeric Borrel

We report an azido-alkynylation of alkenes allowing a straightforward access to homopropargylic azides by combining hypervalent iodine reagents and alkynyl-trifluoroborate salts. The design of a photocatalytic redox-neutral radical polar crossover process ...

2023

Indole Alkaloids Synthesis via a Selective Cyclization of Aminocyclopropanes

Jérôme Waser, Filippo De Simone

The continuous progress in medicinal chemistry requires more versatile synthetic strategies for the generation of large libraries of active compounds and their analogues. As a result, the research for new effective cyclization and cycloaddition reactions i ...

2012

Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes

Jérôme Waser, Stefano Nicolai, Raha Sedigh-Zadeh

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this ...

American Chemical Society2013

Catalytic Formal Homo-Nazarov Cyclization

Jérôme Waser, Julien Alexandre Andres, Filippo De Simone

The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic and carbocyclic compounds were obtained under mild conditions using Brønsted acid ca ...

American Chemical Society2009

Raw data for article "Iron-catalyzed synthesis of α-azido α-amino esters via the alkylazidation of alkenes"

Jérôme Waser, Pierre Gérard Joseph Palamini, Emmanuelle Madeline Dominique Allouche

Raw NMR, IR and MS data for the article "Iron-catalyzed synthesis of α-azido α-amino esters via alkylazidation of alkenes" published in Org. Lett. The number of the folders either correspond to compounds numbers in the article or the name of the folder is ...

Zenodo2023

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Oleksandr Liashuk, Jérôme Waser

A photochemical [2+2] cycloaddition of alkynyl boronates and maleimides is reported. The developed protocol provided 35–70 % yield of maleimide-derived cyclobutenyl boronates and demonstrated wide compatibility with various functional groups. The synthetic ...

2023

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Jérôme Waser, Matthew Wodrich, Paola Caramenti, Nina Declas, Romain Gaëtan Tessier

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Matthew Wodrich, Stefano Nicolai, Durga Prasada Rao Hari, Eliott Hugo Joran Le Du, Nieves Pilar Ramirez Hernandez

First synthesized in 1991, EthynylBenziodoXolones (EBXs) - cyclic hypervalent iodine reagents derived from 2-iodobenzoic acid - are now among the most versatile electrophilic alkynylation reagents. Due to their cyclic structure, these reagents exhibit enha ...

WILEY-V C H VERLAG GMBH2023

Synthesis of (Carbo) nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Sophie Lucie Racine, Eloísa Sofía Serrano Robledo

(Carbo) nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-accep ...

Wiley-Blackwell2014

Forging 1,1′-Bicyclopropenyls by Synergistic Au/Ag Dual-Catalyzed Cyclopropenyl Cross-Coupling

Jérôme Waser, Xiangdong Li

1,1′-Bicyclopropenyl is a constitutional isomer of benzene comprising two coupled cyclopropene units with the endocyclic double bonds in conjugation. Due to the intrinsic high strain energy, it remains a long-standing challenge to prepare 1,1′bicyclopropen ...

American Chemical Society (ACS)2024

N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

Jérôme Waser, Raphaël Michel Henri Simonet-Davin, Emmanuelle Madeline Dominique Allouche

A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at th ...

2022

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

Jérôme Waser, Julien Aymeric Borrel

We report the detailed background for the discovery and development of the synthesis of homopropargylic azides by the azidoalkynylation of alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in a 29% yield of the desi ...

Beilstein-Institut2024

Ficini Reaction with Acrylates for the Stereoselective Synthesis of Aminocyclobutanes

Jérôme Waser

The first Ficini reaction between ynamides and acrylates is reported herein. The reaction is catalyzed by B(C6F5)3 acting as a Lewis acid and is giving access to stable tri-substituted aminocyclobutenes in high yield. The resulting products can be hydrogen ...

Wiley2024

Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

Shyamal Chakrabarty, Jérôme Waser, Johannes Preindl

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...

2017

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Jérôme Waser, Filippo De Simone

The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with amin ...

2011

In the Lab Combining Catalyst and Reagent Design for Electrophilic Alkynylation Johnson Matthey Technology Review features new laboratory research

Jérôme Waser

Johnson Matthey Publ Ltd Co2015

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

Jérôme Waser, Christian Heinis, Xinjian Ji, Xingyu Liu

Swiss Chemical Soc2023