Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis
Abstract Benzo[1,3,2]dithiazole‐1,1,3‐trioxides are bench‐stable and easy‐to‐use reagents. In photoredox catalysis, they generate methyl and perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, and N ‐Ts acrylamide. As byproduct, a salt is formed which can be regenerated to the original methylating agent. Flow chemistry provides an option for reaction scale‐up further underscoring the synthetic usefulness of these methylation reagents. Mechanistic investigations suggest a single‐electron transfer (SET) pathway induced by photoredox catalysis.
Authors
- Carsten Bolm (ORCID: https://orcid.org/0000-0001-9415-9917)
- Guillaume Dagousset (ORCID: https://orcid.org/0000-0001-8720-3828)
- Bruce Pégot (ORCID: https://orcid.org/0000-0001-5137-5548)
- Elsa Anselmi (ORCID: https://orcid.org/0000-0003-2996-2775)
- Peng Wu (ORCID: https://orcid.org/0000-0002-5204-0229)
- Emmanuel Magnier (ORCID: https://orcid.org/0000-0003-3392-3971)
- Gabriel Goujon
- Béatrice Tuccio (ORCID: https://orcid.org/0000-0002-3777-0549)
- Shulei Pan
Institutions
- Université de Tours (FR)
- Centre National de la Recherche Scientifique (FR)
- Aix-Marseille Université (FR)
- Université Paris-Saclay (FR)
- Institut de Chimie Radicalaire (FR)
- Institut Lavoisier de Versailles (FR)
- RWTH Aachen University (DE)
Publication Details
- Journal
- Angewandte Chemie
- Published
- 2024-09-05
- DOI
- https://doi.org/10.1002/ange.202412418
- Citations
- 2
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50