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Jérôme Waser

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Publications associées (189)

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

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

Matthew Wodrich, Jérôme Waser, Franck Le Vaillant

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and no ...

2017

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

Jérôme Waser, Stefano Nicolai, Thibaut Christian Courant, Franck Le Vaillant, Sébastien Pierre Louis Alazet

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of ca ...

2017

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

Jérôme Waser, Shyamal Chakrabarty, 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

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

Jérôme Waser, Jonathan Brand, Gergely Laszlo Tolnai

The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a car ...

2016

Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation

Jérôme Waser, Maria Victoria Vita, Yifan Li, Durga Prasada Rao Hari

Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their ...

Wiley-Blackwell2016

Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis

Jérôme Waser

In this review, a personal account of our work in the field of hypervalent iodine reagents is presented. Pioneering experiments, which led to the discovery of the exceptional reactivity of EthynynnnlBenziodoXol( on)e (EBX) reagents as electrophilic alkyne ...

2016

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination

Jérôme Waser, Ugo Jonathan Orcel

A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formatio ...

Wiley-VCH Verlag GmbH2016

Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor-Acceptor Cyclopropanes

Rosario Scopelliti, Jérôme Waser, Sophie Lucie Racine, Bence Márton Hegedüs

Efficient methods for the convergent synthesis of (poly) cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor-acceptor cyclopropanes, which ...

Wiley-Blackwell2016

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: alpha- or beta- pi-Addition?

Matthew Wodrich, Jérôme Waser, Paola Caramenti

The alkynylation of thiols with EthynylBenziodoXolone (EBX) reagents is a fast and chemoselective method for the synthesis of thioalkynes. Combined experimental and computational studies are reported, which led to the identification of a new mechanism for ...

2016

Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents

Jérôme Waser, Durga Prasada Rao Hari

Alkynes have found widespread applications in synthetic chemistry, biology, and materials sciences. In recent years, methods based on electrophilic alkynylation with hypervalent iodine reagents have made acetylene synthesis more flexible and efficient, but ...

American Chemical Society2016

Nucleoside Analogues: Synthesis from Strained Rings

Jérôme Waser, Sophie Lucie Racine, Jérémy Vuilleumier

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

Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

Jérôme Waser, Thibaut Christian Courant, Franck Le Vaillant

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes fro ...

Wiley-Blackwell2015

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

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

Intramolecular palladium-catalyzed alkene carboalkynylation

Jérôme Waser, Stefano Nicolai, Peter Swallow

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

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

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

General and Practical Formation of Thiocyanates from Thiols

Matthew Wodrich, Jérôme Waser, Reto Frei, Thibaut Christian Courant

A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad ...

Wiley-Blackwell2015

1-Alkynyltriazenes as Functional Analogues of Ynamides

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

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

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