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Jérôme Waser

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Related publications (189)

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, Lionel Schouwey, Durga Prasada Rao Hari, Paola Caramenti, 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

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

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

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

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Rosario Scopelliti, Jérôme Waser, Lionel Schouwey, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Verity Barber

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

An Alternative One-Electron Oxidation Strategy to Access Hypervalent Iodine Reagents

Jérôme Waser, Marion Marie-Agnès Garreau

In this issue of Chem, Powers and co-workers demonstrate that iodanyl radicals are the key oxidants and chain carriers in a proposed open-shell mechanism for the aerobic synthesis of hypervalent iodine compounds. ...

2019

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

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal ca ...

Wiley-VCH Verlag GmbH2019

Revisiting the Urech Synthesis of Hydantoins: Direct Access to Enantiopure 1,5-Substituted Hydantoins Using Cyanobenziodoxolone

Jérôme Waser, Franck Le Vaillant, Nina Declas

A method for the synthesis of enantiopure 1,5-substituted hydantoins was developed using a hypervalent iodine cyanation reagent (cyanobenziodoxolone, CBX) as a source of electrophilic carbon. Starting from inexpensive commercially available enantiopure pro ...

2019

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Thierry Meyer, Jérôme Waser, Stefano Nicolai, Raphaël Michel Henri Simonet-Davin, Annik Nanchen, Sébastien Pierre Louis Alazet, Johannes Preindl

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, ...

2018

Fine-Tuned Organic Photoredox Catalysts for Fragmentation-Alkynylation Cascades of Cyclic Oxime Ethers

Jérôme Waser, Stefano Nicolai, Ganna Gryn'ova, Franck Le Vaillant, Marion Marie-Agnès Garreau

2018

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

Jérôme Waser, Paola Caramenti, Raj Kumar Nandi

2018

Cyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung

Jérôme Waser, Durga Prasada Rao Hari, Paola Caramenti

2018

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

Jérôme Waser, Paola Caramenti, Erwann Stefan Grenet, Ashis Kumar Das

2018

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor Meso-Diaminocyclopropanes

Jérôme Waser, Daniele Perrotta, Mingming Wang

Wiley-VCH Verlag GmbH2018

Iridium- and Rhodium-Catalyzed Directed C–H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents

Jérôme Waser, Erwann Stefan Grenet

2018

Palladium-Catalyzed Carboamination of Allylic Alcohols Using a Trifluoroacetaldehyde-Derived Tether

Jérôme Waser, Ugo Jonathan Orcel, Bastian Antoine Rodolphe Claude Muriel

The selective palladium-catalyzed carboamination of allylic alcohols is reported on the basis of the use of an easily introduced trifluoroacetaldehyde-derived tether. Aminoalkynylation reactions were realized using alkynyl bromides and commercially availab ...

2017

Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents

Jérôme Waser, Franck Le Vaillant

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild cond ...

2017

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

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

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

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

In situ tether formation from amines and alcohols enabling highly selective Tsuji-Trost allylation and olefin functionalization

Jérôme Waser, Ugo Jonathan Orcel

The use of tethers allows to overcome reactivity and selectivity issues often encountered with intermolecular reactions. Although tethers have been successfully applied for decades, their installation and removal usually requires additional steps. This min ...

2017

Gold-catalyzed domino cyclization-alkynylation reactions with EBX reagents: new insights into the reaction mechanism

Jérôme Waser, Yifan Li, Paola Caramenti

Gold-catalyzed domino processes constitute a useful alternative to C-H functionalization for the synthesis of functionalized (hetero)arenes. Herein, we report computational studies on the gold-catalyzed cyclization alkynylation of keto-allenes with ethynyl ...

2017

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