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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.

SUBMITTER: Maity S

PROVIDER: S-EPMC9972470 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Maity Subrata S Szpilman Alex M AM

Organic letters 20230213 7

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. Mechani ...[more]

PMID: 36779928

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