“Green” Oxidant (Oxygen) Mediated Synthesis of <i>N</i>-(2-(Methylsulfonyl)ethyl)amide Derivatives Using DMSO as a Dual Synthon and Solvent
Sulfone derivatives are important components of many pharmaceuticals. This Letter reports an efficient method for synthesizing <i>N</i>-(2-(methylsulfonyl)ethyl)amide compounds with sulfone skeletons from amide compounds and dimethyl sulfoxide (DMSO) using an environmentally benign oxidant (oxygen). This metal-free protocol features operational simplicity, a low-cost and nonhazardous oxidant mediator, good functional group tolerance, and scalability to gram-scale. Notably, DMSO acts as a dual synthon donor, providing both methylene (-CH<sub>2</sub>-) and methylsulfonyl (-SO<sub>2</sub>Me) groups to form C(sp<sup>3</sup>)-N and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bonds while serving as the solvent. A radical mechanism is proposed based on control experiments and EPR spectroscopy.
Authors
- Hui Wu (ORCID: https://orcid.org/0000-0002-3068-3805)
- Hu Cai (ORCID: https://orcid.org/0000-0003-2372-3319)
- Yongfa Xie (ORCID: https://orcid.org/0000-0001-5004-5483)
- Siming Gong
- Changlong Zhuo
Institutions
- Nanchang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-02
- DOI
- https://doi.org/10.1021/acs.orglett.5c03851
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94