Base-Catalyzed Lossen Rearrangement: Modular Synthesis of α-Fluoroamides
Herein, we have developed a cascade reaction, which constructs C-N, C-C, and C-F bonds in a one-pot process through a base-catalyzed Lossen rearrangement of dioxazolones. The key to the success of this process lies in utilizing the base-catalyzed Lossen rearrangement of dioxazolones and the zwitterionic nature of the phosphorus ylides. This cascade reaction protocol integrates C-F bond formation and amide bond formation into a single process, enabling the efficient preparation of a wide range of structurally diverse α-fluoroamides. These compounds are otherwise difficult to obtain through such a modular approach using alternative methods.
Authors
- Linfeng Song (ORCID: https://orcid.org/0000-0002-3502-3574)
- Shiyang Hou (ORCID: https://orcid.org/0000-0002-6583-8758)
- Haiqing Yang (ORCID: https://orcid.org/0000-0003-4497-044X)
- Yanxiao Cao (ORCID: https://orcid.org/0000-0001-7165-3285)
- Yifei Liu (ORCID: https://orcid.org/0000-0002-4821-2067)
- Feng Li (ORCID: https://orcid.org/0000-0003-2846-4440)
- Shuai Zhou (ORCID: https://orcid.org/0000-0001-7236-7563)
- Xueting Cai (ORCID: https://orcid.org/0000-0002-1390-4629)
- Chong Li (ORCID: https://orcid.org/0009-0000-3015-181X)
Institutions
- Zaozhuang University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-03
- DOI
- https://doi.org/10.1021/acs.joc.5c02026
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79