Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism
A detailed study of the reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF<sub>3</sub>-isoxazoles. The chemoselectivity of the reaction w...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-11-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/23/23/14522 |
| Summary: | A detailed study of the reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF<sub>3</sub>-isoxazoles. The chemoselectivity of the reaction was switchable via acid catalysis. The reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> in EtOH produced high yields of 4-trifluoroacetyltriazoles. In contrast, the formation of 5-CF<sub>3</sub>-isoxazoles was observed under catalysis by acids. This acid-switchable procedure can be performed at sub-gram scale. The possible reaction mechanism was supported by DFT calculations. The synthetic utility of the prepared 4-trifluoroacetyltriazoles was demonstrated. |
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| ISSN: | 1661-6596 1422-0067 |