Department of Chemical Sciences, Ariel University, Ariel 4070000, Israel.
Org Lett. 2023 Feb 24;25(7):1218-1222. doi: 10.1021/acs.orglett.3c00313. Epub 2023 Feb 13.
Several methods have been reported for the formation of 2-fluoroenones. However, all these methods involve laborious multiple-step sequences with resulting low overall yields. In this paper, we report the first formal enone-α-H to F substitution, leading to 2-fluoroenones in a single step from ubiquitous enones in 63-90% yield. The reaction is applicable to a wide range of aromatic and alkenyl enones and is carried out at room temperature using HF-pyridine complex as the fluoride source. Mechanistic investigations support that the reaction takes place through a rare umpolung Morita-Baylis-Hillman-type mechanism.
已经有几种方法被报道用于 2-氟烯酮的形成。然而，所有这些方法都涉及繁琐的多步序列，导致最终的总收率较低。在本文中，我们报告了首例正式的烯酮-α-H 到 F 的取代反应，通过 HF-吡啶络合物作为氟源，在室温下以 63-90%的收率从普遍存在的烯酮一步得到 2-氟烯酮。该反应适用于广泛的芳香族和烯基烯酮，并且通过一个罕见的反转 Morita-Baylis-Hillman 型反应机理进行。
