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.
Original language | English |
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Pages (from-to) | 1218-1222 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 25 |
Issue number | 7 |
DOIs | |
State | Published - 24 Feb 2023 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry