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- Title
Transition Metal-Free Direct Trifluoromethylation of 2,3-Dihydropyridin-4(1 H)-ones at Room Temperature.
- Authors
Yu, Yi ‐ Yun; Ranade, Adwait R.; Georg, Gunda I.
- Abstract
A transition metal-free, regioselective C-5 trifluoromethylation of 2,3-dihydropyridin-4(1 H)-ones (cyclic enaminones) with trimethyl(trifluoromethyl)silane (TMSCF3) was developed that proceeds under mild conditions at room temperature. This direct transformation was successful with both electron-rich and electron-deficient cyclic enaminones. This method bypasses substrate prefunctionalization and transition metal catalysis, and allows the convenient and direct access to a variety of medicinally important 3-trifluoromethylpiperidine derivatives. This chemistry also represents a rare example of a direct trifluoromethylation of an internal olefinic CH bond. A radical mechanism is proposed for this reaction.
- Subjects
CHEMICAL reagents; CYCLIC compounds synthesis; TRANSITION metal compounds synthesis; CARBON-hydrogen bonds; HETEROCYCLIC compounds synthesis; CHEMICAL reactions
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 17, p3510
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201400417