Synthesis of β-fluoroenones and their reductive rearrangement in aqueous media

A simple and direct method for the Claisen-Schmidt reaction to prepare functionalized α,β-unsaturated ketones has been developed. Microwave irradiation of aldehydes with acetone produces benzalacetones selectively without self-condensation product in very short reaction times and good yields.Graphical AbstractGraphics for use in the Table of Contents.Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-015-0985-8) contains supplementary material, which is available to authorized users.

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“…Yield : 56.1 mg (85%), R f = 0.49 SiO 2 (cyclohexane/EtOAc : 8/2). NMR data are in agreement with those previously reported (He et al 2013 ).…”

Section: Resultssupporting

confidence: 93%

An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

2015

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“…The hydrofluorination of allenyl ketones was studied by Fan and co-workers in 2013; the transformation was carried out in aqueous media with TBAF•3H 2 O as the fluoride source resulting in β-fluoroenones (Scheme 170). 170 The reaction displayed good selectivity towards formation of the E isomer.…”

Section: Allenes and Derivativesmentioning

confidence: 95%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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“…Treating allenic ketone 1 with TBAFÁ3H 2 O in water afforded b-fluoro-a,b-unsaturated ketone 69 in a regioselective manner with good efficiency (Scheme 35). [29] Interestingly, treating 69 with KBH 4 in aqueous media afforded (E)-4-phenylbut-3-en-2-one (70) rather than the b-fluoroalcohol, most likely through a rearrangement process via the intermediates 71, 72, and 73, as demonstrated in Scheme 36.…”

Section: Reactions Of 12-allenic Ketones With F-nucleophilesmentioning

confidence: 99%

“…Fluoroenones play an important role in both organic and pharmaceutical chemistry due to their unique properties and diverse reactivities. Treating allenic ketone 1 with TBAF·3H 2 O in water afforded β‐fluoro‐α,β‐unsaturated ketone 69 in a regioselective manner with good efficiency (Scheme ) 29…”

Section: Reactions Of 12‐allenic Ketonesmentioning

confidence: 99%

“…[23] 2H-Quinolizin-2-ones have been identified as potential anti-HCV drugs targeting NS5B polymerase or as p38a MAP kinase inhibitors. By using 1-phenylpenta-3,4-dien-2-one (23) and pyridine (29) as the substrates, a novel and green methodology for the synthesis of 3,4-dihydroquinolizin-2-one 55 was developed. Notably, the reaction was carried out at room temperature in aqueous ethanol, and involved a convenient workup of simple precipitation and filtration.…”

Section: Reactions Of 12-allenic Ketones With N-nucleophilesmentioning

confidence: 99%

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Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

Fan

Zhang

2016

The Chemical Record

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This Personal Account summarizes our recent efforts in searching for novel synthetic strategies for a number of organic molecules by using allene derivatives as valuable substrates. It starts with a concise description of the background of allene-related synthetic chemistry. The second part deals with the reactions of 1,2-allenic ketones, including the reactions of 1,2-allenic ketones with various nucleophiles to afford functionalized benzenes, heterocycles, and fluoroenones, and those of allenic ketones as nucleophiles under the promotion of bases to provide 1,3,4'-triones or functionalized furans. The third part of this account focuses on the reactions of α-allenic alcohols. In this section, multicomponent reactions involving α-allenic alcohols, and cascade reactions of α-allenic alcohols promoted by Brønsted acid or iodine, are presented.

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Synthesis of β-fluoroenones and their reductive rearrangement in aqueous media

Cited by 15 publications

References 56 publications

An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

Synthesis of Monofluoroalkenes: A Leap Forward

Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

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