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Jérôme Waser

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Publications associées (186)

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

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

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 Functionalization of Heterocycles with EBX Reagents: C-H Alkynylation versus Deconstructive Ring Cleavage

Jérôme Waser, Marion Marie-Agnès Garreau

The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C-H functionalization of saturated O-heterocycles, as well as the deconstru ...

2020

Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents

Jérôme Waser, Nina Declas

We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, eas ...

Wiley-VCH Verlag GmbH2020

Pd-Catalyzed Intramolecular Oxyalkynylation of Alkenes with Hypervalent Iodine

Jérôme Waser, Stefano Nicolai, Davinia Fernández González

The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solve ...

American Chemical Society2010

Enantioselective Synthesis of Polycyclic Carbocycles via an Alkynylation-Allylation-Cyclization Strategy

Jérôme Waser, Pascal Miéville, Maria Victoria Vita

A new general three-stage strategy to access polycyclic ring systems bearing all-carbon quaternary centers with high enantioselectivity is reported. The required starting materials were readily accessed in racemic form through the alpha-alkynylation of ket ...

American Chemical Society2014

Intramolecular palladium-catalyzed alkene carboalkynylation

Jérôme Waser, Stefano Nicolai

Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compoun ...

Elsevier2015

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole Transport Properties

Jérôme Waser, Anne-Clémence Corminboeuf, Kevin Sivula, Xavier Adrian Jeanbourquin, Ganna Gryn'ova, Yifan Li, Felipe Andres Saenz Padilla

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still chall ...

2017

A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine

Jérôme Waser, Stefano Nicolai, Cyril Piemontesi

Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, ...

Wiley-VCH Verlag GmbH2011

Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives

Jérôme Waser, Eliott Hugo Joran Le Du, Emma Gabrielle Louise Robert

An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine(iii) diacetate (PIDA) in combination with BF3 center dot OEt2. The reaction gives access to a variety of valuable ...

Royal Society of Chemistry2022

Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines

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

With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yield ...

Wiley-VCH Verlag GmbH2011

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

Jérôme Waser, Stefano Nicolai, Paola Caramenti

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 degrees C and were applied in the C-H arylation of unactivated arene ...

2017

Copper-Catalyzed Oxyalkynylation of C-S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents

Jérôme Waser, Guillaume Dominique Pisella, Julien Aymeric Borrel

We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most ...

2019

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Jérôme Waser, Matthew Wodrich, Xiangdong Li

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

2024

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Jérôme Waser, Paola Caramenti, Maria Victoria Vita

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladiumcatalyzed decarboxylative allylation of alpha-azido and cyano beta-ketoesters is reported. Indano ...

American Chemical Society2015

Tandem Photoredox and Copper-Catalyzed Decarboxylative C(sp3)–N Coupling of Anilines and Imines Using an Organic Photocatalyst

Xile Hu, Jérôme Waser, Runze Mao, Marion Marie-Agnès Garreau, Guido Barzanò

An organic photoredox catalyst, 4CzIPN, was used in combination with a copper catalyst, CuCl, to effect decarboxylative C(sp3)–N coupling. The coupling worked with both anilines and imines as nitrogen sources and could be used to prepare a variety of alkyl ...

2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Jérôme Waser, Marion Marie-Agnès Garreau, Stephanie Grace Elizabeth Amos, Luca Buzzetti

Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy finetuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this revi ...

2020

Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions

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

In this Letter, we describe the synthesis of new donor-acceptor substituted cyclopropanes bearing various imido groups and their use in [3+2]-annulation reactions. A sequence of palladium-catalyzed vinylation and rhodium-catalyzed cyclopropanation gave acc ...

Georg Thieme Verlag2014

1-Alkynyltriazenes as Functional Analogues of Ynamides

Rosario Scopelliti, Kay Severin, Jérôme Waser, Gregor Kiefer, Loïc Nicolas Jeanbourquin, Sophie Lucie Racine, Daniele Perrotta, Florian Gérald Abela

The chemical reactivity of 1-alkynyltriazenes has been investigated and is found to parallel the reactivity of ynamides. The similarity in reactivity of these two classes of compounds is demonstrated by addition reactions with acids, by cycloaddition react ...

Wiley-Blackwell2015

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Jérôme Waser, Durga Prasada Rao Hari

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usin ...

2017

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

Jérôme Waser, Fides Benfatti, Florian Patrick Marie Daniel De la Barre De Nanteuil, Reto Frei, Filippo De Simone, Eloísa Sofía Serrano Robledo

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subcl ...

Royal Society of Chemistry2014