Monofluorination of Organic Compounds: 10 Years of Innovation

Champagne, Pier Alexandre; Desroches, Justine; Hamel, Jean‐Denys; Vandamme, Mathilde; Paquin, Jean‐François

doi:10.1021/cr500706a

Cited by 807 publications

(336 citation statements)

References 750 publications

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“…The deoxofluorinating reaction is a modified nucleophilic fluorinating reaction which involves the generation of an activated alcohol as well as a fluoride ion. 7 The fluoride ion participates in a nucleophilic attack, generally an SN2 reaction, to produce an alkyl fluoride (Scheme 2). With this form of selective fluorination, many deoxofluorinating reagents have been developed.…”

Section: Scheme 1 Nucleophilic Fluorination Reactionmentioning

confidence: 99%

Selective fluorination of natural products

Luzzio¹,

Monsen²,

Zhdankin³

2017

Arkivoc

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Compounds derived from natural sources including animals, plants, and micro-organisms have been widely used for pharmaceuticals, materials, and agrochemicals. The use of these natural products has grown increasingly over the years and the demand for more improved, biologically active, and safer derivatives of natural products has been investigated by many researchers in the areas of synthetic and medicinal chemistry. Due to the unique characteristics of fluorinated compounds, and the increased or more favorable biological activity which usually accompanies fluorinated analogues of medicinally-important compounds, the fluorination of natural products has gained much attention. This review aims at exploring the range of specific natural product types that have been selectively fluorinated as well as how fluorination was expected to affect their biological activities and physiochemical properties.

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Section: Scheme 1 Nucleophilic Fluorination Reactionmentioning

confidence: 99%

Selective fluorination of natural products

Luzzio¹,

Monsen²,

Zhdankin³

2017

Arkivoc

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“…The unique properties of the fluorine atom, such as high electronegativity, low polarizability, and small covalent radius together with the great strength of the C-F bond and its tendency to increase lipophilicity of organic molecules are behind its wide impact. Circa 30−40% of agrochemicals and 20% of pharmaceuticals contain at least one fluorine atom [2,3].…”

Section: Introductionmentioning

confidence: 99%

“…Many perfluoroheteroaromatic compounds such as perfluoroquinoline [4] and pentafluoropyridine, in which all the hydrogen atoms of the heterocyclic rings have been replaced by fluorine atoms, have been investigated since the early 1960s [2,5,6]. The most important reaction of pentafluoropyridines involves the replacement of the para-fluorine atom by nucleophilic reagents allowing the synthesis of new organofluorine compounds such as heterocyclic and macrocyclic perfluoro systems [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Crystal Structure of 1,4,5,8-Tetrakis(Perfluoropyridin4-yloxy) Naphthalene

Beyki¹,

Kaminsky²,

Heydari³

et al. 2017

Struct Chem Crystallogr Commun

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1,4,5,8-tetrakis(perfluoropyridin-4-yloxy)naphthalene (tetra-PPN) was synthesized via a one-pot pseudo-five-component reaction of pentafluoropyridine and 5,8-dihydroxy-1,4-tetralindione under basic conditions in DMF. The asymmetric unit contains one half-mol ecule of tetra-PPN and data reveals that half of the molecule being related to the other via inversion symmetry. A detailed analysis of the intermolecular interactions of the compound has been performed using Hirshfeld surfaces. The optimized geometrical parameters and calculated spectroscopic features obtained by quantum chemical calculations using density functional (DFT) methods. In addition, to support the experimental results, the 19F NMR values are obtained using B3LYP method. The obtained results are compared with experimental values show a very good agreement with the experimental data.

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“…In view of the significance of a fluorine atom in an organic molecule, epoxide opening with fluoride, without doubt, is a highly useful approach for the introduction of a fluorine atom into a certain molecule [11][12][13]. Numerous synthetic approaches including asymmetric methodologies have been developed for epoxide opening with fluoride.…”

Section: Introductionmentioning

confidence: 99%