Publications de Jérôme Waser

Photomediated aliphatic C-H functionalization

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 ...

NATURE PORTFOLIO2025

Enantioselective Synthesis of 1,2-disubstituted Thiocyclobutanes via Michael Addition

Jérôme Waser, Emma Gabrielle Louise Robert

We report the diastereoselective and enantioselective synthesis of thio-substituted cyclobutanes via a sulfa-Michael addition using cyclobutenes. In the presence of DBU, various thio-cyclobutane esters and amides were obtained in up to quantitative yield a ...

ROYAL SOC CHEMISTRY2025

Beginning of Second Mandate as Editors-in-Chief for Helvetica Chimica Acta

Jérôme Waser

The beginning of 2025 marks the completion of our first 3-year mandate as Editors-in-Chief of Helvetica Chimica Acta. This has been an exciting and intensive period of time, which has allowed us to drive forward our vision for the journal. We are now delig ...

2025

Unlocking σ-Type Cyclopropenium Cation Transfer Reactions by an Iodine(III)-Based Umpolung Strategy

Jérôme Waser, Xiangdong Li

sigma-Type cyclopropenium cations (CPCs), which are formally generated by removing one substituent on the alkene of cyclopropenes, represent promising intermediates for forging functionalized cyclopropenes. However, sigma-type CPCs are challenging to acces ...

GEORG THIEME VERLAG KG2025

Synthesis of Bicyclo[1.1.1]pentane Z‐Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents

Jérôme Waser, Elija Grinhagena

Bicyclo[1.1.1]pentanes (BCPs) are well‐studied bioisosteres for para‐substituted benzene rings and numerous methods for synthesizing 1,3‐difunctionalized BCPs have been developed. However, synthetic approaches to access vinyl BCP motifs remain limited, wit ...

Wiley2025

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

Anne-Sophie Chauvin, Jérôme Waser, Beat Fierz, Xingyu Liu, Wei Cai

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 ...

Wiley2025

The Azidofunctionalization of Alkenes

Jérôme Waser, Pierre Gérard Joseph Palamini

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, ...

Wiley2025

Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover

Jérôme Waser, Pierre Gérard Joseph Palamini, Alexandre Alain Schöpfer

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, ...

Wiley2025

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Matthew Wodrich, Jérôme Waser, Xiangdong Li

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

2024

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

Jérôme Waser, Emma Gabrielle Louise Robert

: 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 ...

Swiss Chemical Soc2024

Enamine Synthesis via Regiocontrolled 6-endo-dig and 5-exo-dig Tethered Carboamination of Propargylic Alcohols

Jérôme Waser, Mikus Purins, Lucas Antoine Théo Eichenberger

Enamines are versatile building blocks for the synthesis of biologically active compounds. Nevertheless, only a limited number of strategies have been reported for preparing trisubstituted enamines in a regio-and stereoselective manner. Herein, we report a ...

Wiley2024

Organic Dye Photocatalyzed Synthesis of Functionalized Lactones and Lactams via a Cyclization-Alkynylation Cascade

Jérôme Waser, Diana Cavalli

An organic dye photocatalyzed lactonization-alkynylation of easily accessible homoallylic cesium oxalates using ethynylbenziodoxolone (EBX) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up to 88% y ...

2024

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

Jérôme Waser, Nieves Pilar Ramirez Hernandez

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 ...

Georg Thieme Verlag2024

Cost-informed Bayesian reaction optimization †

Anne-Clémence Corminboeuf, Jérôme Waser, Rubén Laplaza Solanas, Alexandre Alain Schöpfer, Jan Weinreich

Bayesian optimization (BO) is an efficient method for solving complex optimization problems, including those in chemical research, where it is gaining significant popularity. Although effective in guiding experimental design, BO does not account for experi ...

Royal Society of Chemistry (RSC)2024

Platinum-Catalyzed Isomerization of Cyclopropenes to 1,3-Dienes

Jérôme Waser, Vladyslav Smyrnov

Herein we report a platinum-catalyzed isomerization of cyclopropenes to 1,3-dienes. Diverse dienylated alcohols were obtained in 42-98 % yield. The synthetic potential of the products was demonstrated by their use in Diels-Alder cycloadditions with various ...

Wiley-VHCA AG2024

Homologation of Alkenyl Carbonyls via a Cyclopropanation/Light-Mediated Selective CÀ C Cleavage Strategy

Matthew Wodrich, Jérôme Waser

We report herein our studies on the direct photoactivation of carbonyl cyclopropanes to give biradical intermediates, leading to selective cleavage of the more substituted carbon-carbon bond. Depending on the substrate structure, extended alkenes were isol ...

Wiley2024

Hypervalent Iodine Amino Acid Building Blocks for Bioorthogonal Peptide Macrocyclization

Jérôme Waser

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 ...

Wiley2024

Forging 1,1′-Bicyclopropenyls by Synergistic Au/Ag Dual-Catalyzed Cyclopropenyl Cross-Coupling

Jérôme Waser, Xiangdong Li

1,1′-Bicyclopropenyl is a constitutional isomer of benzene comprising two coupled cyclopropene units with the endocyclic double bonds in conjugation. Due to the intrinsic high strain energy, it remains a long-standing challenge to prepare 1,1′bicyclopropen ...

American Chemical Society (ACS)2024

Interrupted Polonovski Strategy for the Synthesis of Functionalized Amino Acids and Peptides

Jérôme Waser, Emmanuelle Madeline Dominique Allouche, Christine Alice Jacqueline Marty

The alpha-functionalization of carbamate-protected hydroxylamine glycine derivatives, acting as imine surrogates via an interrupted Polonovski reaction, is described to access functionalized amino acid derivatives. The addition of C, N, O, and S nucleophil ...

2024

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

Anne-Clémence Corminboeuf, Matthew Wodrich, Jérôme Waser, Rubén Laplaza Solanas, Alexandre Alain Schöpfer

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 ...

Amer Chemical Soc2024