Photoinduced Nickel-Mediated Radical Coupling Reaction of Sodium Sulfinates with <i>N</i>-Hydroxyphthalimide Esters
Aryl methyl sulfones represent a privileged structural motif in modern drug discovery due to their diverse biological activities and metabolic stability. However, conventional synthetic approaches for these valuable compounds typically necessitate harsh reaction conditions, including elevated temperatures, strong oxidants, or air-sensitive reagents, which significantly limit their applicability in pharmaceutical synthesis. Herein, we present a novel and efficient strategy for the synthesis of aryl methyl/trideuterated methyl sulfones through nickel-mediated radical coupling, which involves the synergistic combination of methyl radicals generated from <i>N</i>-hydroxyphthalimide (NHP) esters and sulfonyl radicals derived from sodium sulfinates. This protocol establishes a versatile platform for the efficient synthesis of diverse aromatic methyl sulfones and their trideuterated analogues under mild reaction conditions, demonstrating good functional group compatibility and a broad substrate scope.
Authors
- Muliang Zhang (ORCID: https://orcid.org/0000-0002-0415-9444)
- Shi‐Kai Tian (ORCID: https://orcid.org/0000-0002-2938-7013)
- Longyu Wang (ORCID: https://orcid.org/0000-0002-8752-7299)
- Linze Zheng
Institutions
- University of Science and Technology of China (CN)
- Hefei National Center for Physical Sciences at Nanoscale (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-27
- DOI
- https://doi.org/10.1021/acs.joc.5c00793
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- University of Science and Technology of China