Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis
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 International Edition
- Published
- 2024-09-05
- DOI
- https://doi.org/10.1002/anie.202412418
- Citations
- 5
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- China Scholarship Council
- Centre National de la Recherche Scientifique
- RWTH Aachen University
- Université de Versailles Saint-Quentin-en-Yvelines
- National Institute of Environmental Health Sciences