Publications by Jérôme Waser

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We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

Highly efficient protocols for the alkynylation of H-phosphi(na)tes and secondary phosphine oxides with silyl, aryl and alkyl ethynyl-benziodoxolone (EBX) reagents are reported. Alkynyl phosphorus compounds were obtained in 69-93% yield without the need fo ...

United we stand! Cooperative activation of the hypervalent-iodine reagent TIPS-EBX with a gold catalyst and a Brønsted acid allowed the first direct ethynylation of thiophenes at room temperature (see scheme; TFA=trifluoroacetic acid). The obtained ethynyl ...

Alkynes and nitriles are valuable building blocks in organic synthesis and also have multiple applications in chemical biology and materials science. Due to the high availability of tertiary alcohols, developing methods for their conversion into alkynes an ...

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 ...

Bis(trifluoromethylated)benziodoxoles (Bx) are broadly used cyclic hypervalent iodine reagents due to their stability and unique chemical properties. However, current methods to access them require several steps and long reaction times, making their synthe ...

: Leveraging the unique reactivity profile of donor -acceptor aminocyclopropanes and cyclobutanes allows the preparation of complex nitrogen -substituted molecules. While most reports focus on donor -acceptor strained rings with two geminal carbonyl groups ...

Peptide and protein bioconjugation sees ever-growing applications in the pharmaceutical sector. Novel strategies and reagents that can address the chemo- and regioselectivity issues inherent to these biomolecules, while delivering stable and functionalizab ...

We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent o ...

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 ...

The C–H functionalization of inert alkanes has long been one of the most challenging reactions in organic synthesis. Now, the use of hypervalent iodine reagents has enabled the diverse functionalization of various aliphatic C–H bonds under blue light irrad ...

The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. H ...

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scanning ...

The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-su ...

We report herein a radical‐mediated amination of cyclopropenes. The transformation proceeds through a cleavage of the three‐membered ring after the addition of an azide radical on the strained double bond and leads to tetrasubstituted alkenyl nitrile deriv ...

Ethynylbenziodoxol(on)es (EB(X)xs) reagents have emerged as useful reagents for peptide/protein modification due to their versatile reactivity and high selectivity. Herein, we report the successful introduction of ethynylbenziodoxoles (EBxs) on different a ...

Over the last two decades, a renaissance has been witnessed in the research field of donor-acceptor (DA) cyclopropanes. Among all the subclasses of DA cyclopropanes, DA cyclopropanes with an amino group as donor (DA aminocyclopropanes) have drawn particula ...

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 ...

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, ...

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

Jérôme Waser

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Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents

Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS–EBX with Gold and Brønsted Acids

Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones

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

One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(i) precursors

Silylium-Catalyzed Activation of DonorAcceptor Strained Rings and Annulation with Indoles

Cysteine-Cysteine Cross-Conjugation of both Peptides and Proteins with a Bifunctional Hypervalent Iodine-Electrophilic Reagent

Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water

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

Photomediated aliphatic C-H functionalization

Zinc-gold cooperative catalysis for the direct alkynylation of benzofurans

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds

Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization

Donor-Acceptor Cyclopropanes with an Amino Group as Donor

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

Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary