2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones.

Abstract

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.