Meerwein arylation with 3-fluorobutenone

Patrick, Timothy B.; Awasabisah, Dennis

doi:10.1016/j.jfluchem.2009.12.009

Cited by 5 publications

(2 citation statements)

References 9 publications

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“…2-Fluoroenones are interesting compounds with a large potential as building blocks for fluorinated medicines given their reactivity. 2-Fluoroenones undergo asymmetric hydrogenation to give chiral 2-fluoroketones, asymmetric Diels–Alder cycloaddition reactions, , and participate readily in Meerwein arylations as well as conjugate addition reactions with a large variety of nucleophiles . Pannecoucke and Hoveyda demonstrated their conversion into biologically active 2-fluoro allylic amines.…”

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

Maity

Szpilman

2023

Org. Lett.

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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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“…Adding to the known synthetic use of 2-fluoroenones, − we demonstrated two synthetic transformations of 2-fluoroenones (Scheme ). Thus, α-fluoroenone 6 was converted to corresponding alkyl alcohol 41 (full reduction) and allyl alcohol 42 (partial reduction) under Pd–C/H 2 and NaBH 4 , respectively (Scheme ).…”

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confidence: 99%

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

Maity

Szpilman

2023

Org. Lett.

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Radical Arylations

Vaillard

Studer

2012

Encyclopedia of Radicals in Chemistry, Biology and Materials

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This article reports on radical arylations, also highlighting the very important early achievements in this field. Included are the Meerwein arylation and the Pschorr reaction. Intramolecular homolytic aromatic substitutions with aryl radicals and various arene radical acceptors for the formation of biaryls are discussed. Along with reactive aryl radicals, nucleophilic and also electrophilic alkyl radicals can cyclize with arenes providing products of intramolecular homolytic aromatic substitution. Discussion on the mechanism is provided. Moreover, it is shown that this chemistry has been successfully used in complex natural‐products synthesis. A section is devoted to radical aryl migration reactions. Finally, reactions of aryl radicals with olefins are discussed. It is also shown that aryl radicals react efficiently with various heteroatom‐based radical acceptors for aryl‐X bond formation (X = Se, S, Te, B, P).

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Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

2014

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This review gives an overview of the generation of aryl radicals, mediated by transition metals, and their use for the C À H arylation of heteroarenes. The different sources of aromatic derivatives able to generate aryl radicals via a metal-assisted reduction or oxidation are discussed, with a critical view of the developed systems. The radical arylations of nitrogen-, oxygen-or sulfur-containing heterocycles are then described and mechanistic considerations are discussed as well.

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Meerwein arylation with 3-fluorobutenone

Cited by 5 publications

References 9 publications

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

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

Radical Arylations

Transition Metal‐Mediated Direct CH Arylation of Heteroarenes Involving Aryl Radicals

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