Publications de Jérôme Waser

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An asymmetric 3-component reaction between EthynylBenziodoXoles (EBXs), 2,2,2-trifluorodiazoethane and nucleophiles catalyzed by a CuI-BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and a ...

Cyclic hypervalent iodine reagents are now frequently used in synthetic organic chemistry, either as oxidants or group-transfer reagents. Vinylbenziodoxol(on)es (VBXs) bearing alkene substituents have been less investigated than the corresponding trifluoro ...

A photoredox-catalyzed oxidative decarboxylative coupling of small peptides is reported, giving access to a variety of N,O-acetals. They were used as intermediates for the addition of phenols and indoles, leading to novel peptide scaffolds and bioconjugate ...

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 ...

In this short review, we present applications merging the reactivity of cyclic hypervalent iodine reagents with carbenes and carbenoids developed in the last decade. The use of more stable cyclic hypervalent iodine reagents has led to major advances in thi ...

Correction for 'Tyrosine bioconjugation with hypervalent iodine' by Nina Declas et al., Chem. Sci., 2022, 13, 12808-12817, https://doi.org/10.1039/D2SC04558C. ...

The first C2-selective alkynylation of indoles using the hypervalent iodine reagent triisopropylsilylethyny1-1,2-benziodoxol-3(1H)-one (TIPS-EBX) with Pd(II) as a catalyst is described. This convenient and robust method gives a single-step access to substi ...

The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using sc ...

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 ...

We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yie ...

Mild Control: Selective cyclization of aminocyclopropanes on the N1 or C3 positions of indole was achieved by tuning the catalyst and solvent. The new strategy was applied to the formal synthesis of aspidospermidine and the total synthesis of goniomitine i ...

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 ...

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 ...

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most f ...

A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO.SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A br ...

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 ...

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reactio ...

The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of a ...

A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups ...

Improving the synthesis of complex organic molecules is essential for progress in many fields such as medicine, agrochemicals or materials. Since 2007, our laboratory has been focusing on the development of non-classical bond disconnections based on the us ...

Jérôme Waser

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Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines**

Vinylbenziodoxol(on)es: Synthetic Methods and Applications

Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

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

Merging the Reactivity of (Pseudo)cyclic Hypervalent Iodine Reagents and Carbenes or Carbenoids

Tyrosine bioconjugation with hypervalent iodine (vol 13, pg 12808, 2022)

C2-Selective Direct Alkynylation of Indoles

[4+2]-Annulations of Aminocyclobutanes

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

Synthesis of bicyclo[3.1.0]hexanes by (3+2) annulation of cyclopropenes with aminocyclopropanes

Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine

Photocatalytic Decarboxylative Functionalization of Cyclopropenes via Cyclopropenium Cation Intermediates

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

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

One-Pot, Three-Component Arylalkynyl Sulfone Synthesis

Semipinacol Rearrangement of Cyclopropenylcarbinols for the Synthesis of Highly Substituted Cyclopropanes

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines

Catalytic Friedel-Crafts Reaction of Aminocyclopropanes

Taming Hypervalent Bonds and Strained Rings for Catalysis and Synthesis