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Jérôme Waser

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Related publications (189)

Donor-Acceptor Cyclopropanes with an Amino Group as Donor

Over the last two decades, a renaissance has been witnessed in the research field of donor-acceptor (DA) cyclopropanes. Among all the subclasses of DA cyclopropanes, DA cyclopropanes with an amino group as donor (DA aminocyclopropanes) have drawn particula ...

Wiley2024

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

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

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

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

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

Photocatalytic Decarboxylative Functionalization of Cyclopropenes via Cyclopropenium Cation Intermediates

Jérôme Waser, Vladyslav Smyrnov

A photocatalytic decarboxylative functionalization of cyclopropenes is reported. Starting from a broad range of redox‐active ester‐substituted cyclopropenes, cyclopropenylphthalimides can be synthesized in the absence of a nucleophile. Alternatively, diffe ...

Wiley2024

Diastereoselective Synthesis of N-Heterocycle Substituted Cyclobutanes via Michael Addition onto Cyclobutenes

Jérôme Waser, Emma Gabrielle Louise Robert

Herein, we present a method for the diastereoselective synthesis of N-heterocycle-substituted cyclobutanes from commercially available bromocyclobutanes. This method enables the efficient formation of various heterocyclic aminocyclobutane esters and amides ...

Wiley2024

Semipinacol Rearrangement of Cyclopropenylcarbinols for the Synthesis of Highly Substituted Cyclopropanes

Jérôme Waser, Vladyslav Smyrnov

An electrophile-induced semipinacol rearrangement of cyclopropenylcarbinols is reported. This transformation gives access to various polyfunctionalized cyclopropanes under mild metal-free conditions. The scope of the reaction includes iodine, sulfur and se ...

2023

Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization

Aleksandra Radenovic, Jérôme Waser, Beat Fierz, Xingyu Liu, Nathan Cyprien Arsène Ronceray, Wei Cai

Rapid and efficient cyclization methods that form structurally novel peptidic macrocycles are of high importance for medicinal chemistry. Herein, we report the first gold(I)-catalyzed macrocyclization of peptide-EBXs (ethynylbenziodoxolones) via C2-Trp C–H ...

2023

One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(i) precursors

Jérôme Waser, Xingyu Liu, Nieves Pilar Ramirez Hernandez, Tobias Michael Milzarek

Bis(trifluoromethylated)benziodoxoles (Bx) are broadly used cyclic hypervalent iodine reagents due to their stability and unique chemical properties. However, current methods to access them require several steps and long reaction times, making their synthe ...

Royal Society of Chemistry2023

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

Christian Heinis, Jérôme Waser, Xinjian Ji, Xingyu Liu

Swiss Chemical Soc2023

Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles

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

A convenient one-step synthesis of beta-aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocataly ...

Wiley-VCH Verlag GmbH2023

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Jérôme Waser, Oleksandr Liashuk

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

Acyl-Ethynylbenziodoxolone (acyl-EBX): Access to Ketene Dithioarylacetals

Jérôme Waser, Maël Djaïd, Julien Aymeric Borrel, Pierre Gérard Joseph Palamini, Morgane Elodie Marie Delattre

We report the synthesis of ketene dithioarylacetals in 40–97% yield using thiophenols and acyl-EBXs (ethynylbenziodoxolones) generated in situ from a common hypervalent iodine precursor and alkynyl trifluoroborate salts. The products could be further modif ...

2023

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

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

Rosario Scopelliti, Matthew Wodrich, Jérôme Waser, Stefano Nicolai, Farzaneh Fadaei Tirani, 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

The Highly Operational Team (HOT) toward f-Block Materials

Jérôme Waser, Nieves Pilar Ramirez Hernandez

Wiley-VCH Verlag GmbH2023

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

Cysteine-Cysteine Cross-Conjugation of both Peptides and Proteins with a Bifunctional Hypervalent Iodine-Electrophilic Reagent

Jérôme Waser, Stefano Nicolai, Abhaya Kumar Mishra

Peptide and protein bioconjugation sees ever-growing applications in the pharmaceutical sector. Novel strategies and reagents that can address the chemo- and regioselectivity issues inherent to these biomolecules, while delivering stable and functionalizab ...

2023

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

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