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Updated: Aug 10, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones
Subrata Maity1, Alex M Szpilman1
1Department of Chemical Sciences, Ariel University, Ariel 4070000, Israel.
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.
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