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

Subrata Maity, Alex M. Szpilman

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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 languageEnglish
Pages (from-to)1218-1222
Number of pages5
JournalOrganic Letters
Volume25
Issue number7
DOIs
StatePublished - 24 Feb 2023

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