Further studies on the synthesis of α-fluoro carbonyl compounds [1]

Cantrell, Gary L.; Filler, Robert

doi:10.1016/s0022-1139(00)80895-7

Cited by 37 publications

(3 citation statements)

References 21 publications

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“…Since the 1960s till today, the Petrov reagent ( 1a ), the Yarovenko reagent ( 1b ) and the Ishikawa reagent ( 1c ) have been commonly used as selective fluorination agents of compounds containing a hydroxyl moiety, such as alcohols [ 18 , 19 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ], including hydroxyproline [ 50 , 51 , 52 , 53 ] or carbohydrate derivatives [ 54 ], sulfonic [ 19 ] and carboxylic acids [ 55 , 56 , 57 , 58 ]. Interestingly, carbonyl compounds can also react with FARs to afford difluoromethylated compounds [ 59 ].…”

Section: Fluoroalkyl Amino Reagents: Efficient Tools For Fluorinatmentioning

confidence: 99%

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

et al. 2017

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Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)—a class of chemicals that was slightly forgotten over the last decades—has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (hetero)aromatic derivatives.

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Section: Fluoroalkyl Amino Reagents: Efficient Tools For Fluorinatmentioning

confidence: 99%

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

et al. 2017

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“…23 α-Hydroxy acids give α-fluoroacyl fluorides which hydrolyze on workup to form α-fluoro acids. 24 Sulfur tetrafluoride, on the other hand, converts the carboxylic group into a trifluoromethyl group. 21 Reaction with Halides and Sulfonates.…”

mentioning

confidence: 99%

Diethylaminosulfurtrifluoride

Fauq¹,

Singh²,

Meshri³

2006

Encyclopedia of Reagents for Organic Synthesis

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“…Fluorination of an estrone derivative in CH 2 Cl 2 gave a product with a much lower yield (44%) but also with α-stereoselectivity . The ethers of cycloalkanones are reported to give good yields of fluoroketones in CH 2 Cl 2 with a trace of pyridinium poly(hydrogen fluoride) catalyst . We have investigated the TMS enol ethers shown in Table .…”

mentioning

confidence: 99%

Reaction of Silyl Enol Ethers with Xenon Difluoride in MeCN: Evidence for a Nonclassical Radical Cation Intermediate

Ramsden

Smith

1999

Org. Lett.

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The reactions of xenon difluoride in MeCN solution in Pyrex flasks with a series of TMS enol ethers have been investigated. The types of products formed are dependent on the structures of individual enol ethers, but under these conditions all products are consistent with a mechanism involving single electron transfer to un-ionized XeF2 giving a radical cation and subsequent formation of an α-fluoroketone, together with some ketone formation. The results suggest that if the radical cation is particularly stable, fluorodesilylation leads to radical formation, and solvent-derived products are then observed. Using other solvents, such as CFCl3 and C6F6, much more complex mixtures of products are obtained, and this is attributed to a different mode of reaction of xenon difluoride involving ionization to FXe+.

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Further studies on the synthesis of α-fluoro carbonyl compounds [1]

Cited by 37 publications

References 21 publications

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Diethylaminosulfurtrifluoride

Reaction of Silyl Enol Ethers with Xenon Difluoride in MeCN: Evidence for a Nonclassical Radical Cation Intermediate

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