通过 CF-Ynones 与 NaN 反应的酸可切换合成三氟甲基化的三唑和异恶唑：反应机理的 DFT 研究。
Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF-Ynones with NaN: DFT Study of the Reaction Mechanism.
机构信息
Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, Russia.
A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991 Moscow, Russia.
出版信息
Int J Mol Sci. 2022 Nov 22;23(23):14522. doi: 10.3390/ijms232314522.
A detailed study of the reaction of CF-ynones with NaN was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF-isoxazoles. The chemoselectivity of the reaction was switchable via acid catalysis. The reaction of CF-ynones with NaN in EtOH produced high yields of 4-trifluoroacetyltriazoles. In contrast, the formation of 5-CF-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.
对 CF-ynones 与 NaN 的反应进行了详细研究。研究发现，该反应可以选择性地合成 4-三氟乙酰基三唑或 5-CF-异恶唑。通过酸催化可以切换反应的化学选择性。在 EtOH 中，CF-ynones 与 NaN 的反应以高产率生成 4-三氟乙酰基三唑。相比之下，在酸催化下观察到 5-CF-异恶唑的形成。这种酸可切换的程序可以在亚克规模下进行。通过 DFT 计算支持了可能的反应机制。所制备的 4-三氟乙酰基三唑的合成实用性得到了证明。
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