DBU‐Triggered One‐Pot Domino Transformation of Trifluoromethyl Ketones and Dicyanoalkenes into <i>gem</i>‐Difluoroalkenyl <i>γ</i>‐Lactams
The direct conversion of trifluoromethyl ketones to valuable gem ‐difluoroalkenes remains a synthetically useful but underexplored transformation. Herein, we report a base‐catalyzed, one‐pot domino reaction of trifluoromethyl ketones with dicyanoalkenes, enabling formal dual deoxygenation and defluorination. This protocol affords a diverse range of gem ‐difluoroalkenyl unsaturated γ ‐lactams in yields of 62–95% under mild and operationally simple conditions. A proposed mechanism involves a sequential vinylogous aldol reaction, cyclization, rearrangement, and defluorination.
Authors
- Hong Zhou (ORCID: https://orcid.org/0000-0003-2409-784X)
- Fa‐Guang Zhang (ORCID: https://orcid.org/0000-0002-0251-0456)
- Jun‐An Ma (ORCID: https://orcid.org/0000-0002-3902-6799)
- Cheng‐Feng Gao
- Jing Nie (ORCID: https://orcid.org/0000-0002-9116-8858)
- Jian Wang (ORCID: https://orcid.org/0000-0002-3298-6367)
- Feng Li (ORCID: https://orcid.org/0000-0003-3288-4069)
Institutions
- Tianjin University (CN)
- Tianjin Medical University Cancer Institute and Hospital (CN)
- Tianjin Synthetic Material Research Institute (China) (CN)
- Zaozhuang University (CN)
- Tianjin Medical University (CN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2025-08-25
- DOI
- https://doi.org/10.1002/adsc.70090
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- National Natural Science Foundation of China