Publications de Jérôme Waser

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Ethynylbenziodoxolones (EBXs) have recently emerged as potent reagents for the alkynylation of radicals. Their combination with photocatalysis allows the synthesis of valuable alkynes at room temperature. Herein, we discuss two photomediated strategies for ...

Herein, we report a cysteine bioconjugation methodology for the introduction of hypervalent iodine compounds onto biomolecules. Ethynylbenziodoxolones (EBXs) engage thiols in small organic molecules and cysteine-containing peptides and proteins in a fast a ...

We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the gamma or delta po ...

We report the first oxidative C-H alkynylation of arylcyclopropanes. Irradiation of ethynylbenziodoxolone (EBX) reagents with visible light at 440 nm promoted the reaction. By the choice of the aryl group on the cyclopropane, it was possible to completely ...

Chiral ligands are important components in asymmetric homogeneous catalysis, but their synthesis and screening can be both time-consuming and resource-intensive. Data-driven approaches, in contrast to screening procedures based on intuition, have the poten ...

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 ...

One of the major challenges faced by organic chemistry is the efficient synthesis of increasingly complex molecules. Since October 2007, the Laboratory of Catalysis and Organic Synthesis (LCSO) at EPFL has been working on the development of catalytic react ...

Since their discovery in 2012, carbazolyl (iso)phthalonitrile derivatives (Cz(I)PN) have found significant applications as photocatalysts in organic chemistry. Herein, we introduce two efficient methods for incorporating carbazolyl cyanobenzenes into vario ...

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis of ...

Over the last fifteen years, gold has been raised from the status of an inert noble metal to one of the most-often-used catalysts in synthetic chemistry. The functionalization of the triple bond of alkynes has been especially successful in this respect. In ...

The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization ...

A palladium-catalyzed multicomponent reaction of propargylic amines, alkynyl bromides and cesium hydrogen carbonate to access oxazolidinones is reported. In contrast to previous reports, only a slight excess of cesium hydrogen carbonate is used as a surrog ...

The first method for the [3 + 2] annulation of donor acceptor aminocyclopropanes with aldehydes is reported. The reaction is catalyzed by iron trichlorlde on alumina in yields up to 99% and with excellent cis selectivities (up to >20:1) and represents a st ...

Hypervalent iodine compounds are powerful reagents for the development of novel transformations. As they exhibit low toxicity, high functional group tolerance, and stability in biocompatible media, they have been used for the functionalization of biomolecu ...

This report describes a full study of the gold-catalyzed direct alkynylation of indoles, pyrroles, and thiophenes using alkynyl hypervalent iodine reagents, especially the study of the structural requirements of alkynyl benziodoxolones for an efficient ace ...

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. ...

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 ...

The azidofunctionalization of alkenes has emerged as a powerful difunctionalization strategy, expanding the toolbox of synthetic chemistry. This transformation enables the simultaneous installation of an azide and a second functional group onto an alkene, ...

In addition to the well-established nucleophilic alkynylation, the use of electrophilic alkynes can expand tremendously the scope of acetylene transfer reactions. The use of metal catalysis has recently led to a rebirth of this research area. Halogenoalkyn ...

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with ...

Jérôme Waser

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Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

"Doubly Orthogonal" Labeling of Peptides and Proteins

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

Substrate-controlled C-H or C-C alkynylation of cyclopropanes: generation of aryl radical cations by direct light activation of hypervalent iodine reagents

Reaction-Agnostic Featurization of Bidentate Ligands for Bayesian Ridge Regression of Enantioselectivity

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

Cyclopropanes and Hypervalent Iodine Reagents: High Energy Compounds for Applications in Synthesis and Catalysis

Peptide‐Carbazolyl Cyanobenzene Conjugates: Enabling Biomolecule Functionalization via Photoredox and Energy Transfer Catalysis

Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents

Gold-Catalyzed Alkynylation: Acetylene-Transfer instead of Functionalization

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes

Palladium-Catalyzed Carboxy-Alkynylation of Propargylic Amines Using Carbonate Salts as Carbon Dioxide Source

Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans

Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization

Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism

Diamine Synthesis via the Nitrogen-Directed Azidation of sigma- and pi-C-C Bonds

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

The Azidofunctionalization of Alkenes

Electrophilic alkynylation: the dark side of acetylene chemistry

Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism