Base-Mediated Regioselective [3 + 3] Annulation of Alkylidene Malononitriles with Trifluoromethyl Alkenes via Dual C–F Bond Cleavage
A base-mediated regioselective [3 + 3] annulation of alkylidene malononitriles with trifluoromethyl alkenes was described. The reaction proceeds through sequential intermolecular S<sub>N</sub>2' and intramolecular S<sub>N</sub>V-type cyclization by cleaving dual C-F bonds in a trifluoromethyl group, which discriminate multiple carbon-nucleophilic sites using a single base. Various bicycles bearing a monofluorocyclohexene motif were assembled from readily available starting materials under mild conditions via a one-pot cascade approach.
Authors
- Weidi Zeng (ORCID: https://orcid.org/0000-0002-4015-2979)
- Lei Zhou (ORCID: https://orcid.org/0000-0002-8391-8452)
- Mingqiang Li (ORCID: https://orcid.org/0000-0002-5178-4138)
- Ablimit Abdukader (ORCID: https://orcid.org/0009-0004-2750-0192)
- Shaofeng Wu (ORCID: https://orcid.org/0009-0008-8396-1742)
Institutions
- Sun Yat-sen University (CN)
- Xinjiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c02788
- Citations
- 7
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.46
Funders
- Natural Science Foundation of Xinjiang Province
- National Natural Science Foundation of China