A New Method for the Synthesis of Aromatic Sulfurpentafluorides and Studies of the Stability of the Sulfurpentafluoride Group in Common Synthetic Transformations

Bowden, Roy D.; Comina, Paul J.; Greenhall, Martin P.; Kariuki, Benson M.; Loveday, Amanda; Philp, Douglas

doi:10.1016/s0040-4020(00)00184-8

Cited by 117 publications

(94 citation statements)

References 25 publications

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“…Elemental fluorine (10% F 2 in N 2 ), that was used to convert at room temperature aromatic nitrothiols and nitro-methylsulfides into the corresponding SF 5 compounds in moderate yields (Scheme 32) [66]. Remarkable results were achieved by employing micro-reactors for fluorinations that were used to convert bis(m-NO 2 -phenyl)-disulfide and p-NO 2 -phenyl-SF 3 into the corresponding SF 5 compounds at room temperature [67].…”

Section: Scheme 31mentioning

confidence: 99%

“…A number of aromatic SF 5 -compounds were synthesised starting from the meta-and para-nitro SF 5 -precursors, which were initially reduced to the corresponding anilines, and then submitted to a range of different reactions including Sandmayer iodination followed by Sonogashira alkynylation, Suzuki arylation and Heck olefination (Scheme 84) [66]. Interestingly, the authors demonstrated that 4-SF 5 -aniline and 4-CF 3 -aniline show similar stability towards acid hydrolysis, namely treatment with concentrated sulphuric acid at 160 °C leads to hydrolysis of both CF 3 and SF 5 groups.…”

Section: Scheme 83mentioning

confidence: 99%

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Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

198

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The pentafluorosulfanyl group (SF5) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF5-compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF5-group into organic molecules. However, recent synthetic progress, the availability of some SF5-building blocks from commercial suppliers and the discovery of interesting properties of SF5-substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF5-substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000. Object *Cover Letter or Page containing Author DetailsAll of the referees' suggestions have been accepted, with the only exception of Referee's 2 point 5 "Reactions of ArylSF5 systems should be divided into sections …electrophilc substitutions, nucleophilic substitutions, reactions of diazo systems,…" because in that section the chemistry is inherently heterogeneous and we feel that such a subclassification would be very challenging to achieve and would make less homogeneous the discussion of the topic. Molecolare, via Mancinelli 7, 20131 Milano, Italy Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are reviewed in this article, with an emphasis on the work published in the last decade. *Graphical Abstract -Synopsis Highlights We review the synthesis of SF 5 -compounds, with an emphasis on work published after year 2000.  We review the reactivity of SF 5 -substituted organic molecules.  We review the biological properties of SF 5 -substituted drug candidates. Aberdeen, Foresterhill, Aberdeen AB25 2ZD, Scotland, UK; e-mail: m.zanda@abdn.ac.uk b C.N.R.-Istituto di Chimica del Riconoscimento Molecolare, via Mancinelli 7, 20131 Milano, Italy AbstractThe pentafluorosulfanyl group (SF 5 ) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF 5 -compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF 5 -group into organic molecules. However, recent synthetic progress, the availability of some SF 5 -building blocks from commercial suppliers and the discovery of interesting properties of SF 5 -substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000.

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Section: Scheme 31mentioning

confidence: 99%

Section: Scheme 83mentioning

confidence: 99%

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

198

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“…When the cis-compound (1) was reacted in a similar fashion, the product cis-1,4-diacetoxy-2-SF 5 -2-cyclohexene, cis- (2) was produced in 70% yield; mp 139-140 8C. …”

Section: Preparation Of Trans/cis-14-diacetoxy-2-sf 5 -2-cyclohexenementioning

confidence: 99%

“…Into a 50-ml round-bottomed flask equipped with a Teflon stirring bar and three stacked Vigerux columns (air condenser), 3.29 g (10.2 mmol) of trans- (2), and 25 ml of diphenylether were added. The mixture was heated to 265-270 8C (temperature of sand bath); after 15 h, the volatile materials were removed under vacuum by heating the reaction mixture to 100 8C for 7 h and collecting the volatile materials in a À78 8C trap (trap was attached to top of Vigerux columns).…”

Section: Preparation Of Sf 5 C 6 H 5 (3) Via Thermolysis Ofmentioning

confidence: 99%

“…This method employs AgF 2 and diphenyl disulfides in a chlorofluorocarbon solvent and is carried out in a copper vessel. More recently, it has been found that elemental fluorine in various solvents (such as CH 3 CN) can be used to prepare SF 5 -aromatic derivatives such as (3-or 4-nitrophenyl) sulfur pentafluoride in 39-41% yields [2]. A brief overview covering the use of AgF 2 and F 2 is given in a recent article [3].…”

Section: Introductionmentioning

confidence: 99%

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