Publications de Raphaël Michel Henri Simonet-Davin

Benzylic C(sp3)-H Azidation: Copper vs Iron Catalysis

Jérôme Waser, Qian Wang, Jieping Zhu, Raphaël Michel Henri Simonet-Davin, Pierre Gérard Joseph Palamini

The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp(3))-H bond functionalization protocols have been developed relying on this elementary step. We report herein copper- and iron-cata ...

2024

Azidation with Hypervalent Iodine Reagents

Jérôme Waser, Raphaël Michel Henri Simonet-Davin

Georg Thieme Verlag2022

Azide-Containing Hypervalent Iodine Reagents for Biomolecules Functionalization

Raphaël Michel Henri Simonet-Davin

The goal of my PhD was the development of a new method for unselective surface labeling, not substrate-specific, that would give access to direct visualization of any surface interactions. In order to achieve this challenging goal, we wanted to develop a g ...

EPFL2022

N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

Jérôme Waser, Raphaël Michel Henri Simonet-Davin, Emmanuelle Madeline Dominique Allouche

A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at th ...

2022

1‐Azido‐3,3‐dimethyl‐3‐(1H )‐1,2‐benziodoxole

Jérôme Waser, Raphaël Michel Henri Simonet-Davin

Wiley2020

"Doubly Orthogonal" Labeling of Peptides and Proteins

Jérôme Waser, Nora Guidotti, Beat Fierz, Romain Gaëtan Tessier, Raphaël Michel Henri Simonet-Davin

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 ...

2019

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Thierry Meyer, Jérôme Waser, Stefano Nicolai, Raphaël Michel Henri Simonet-Davin, Annik Nanchen, Sébastien Pierre Louis Alazet, Johannes Preindl

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, ...

2018