New 4-pentafluorosulfanyl and 4-perfluoroalkylthio derivatives of 1-chloro-2-nitro- and 1-chloro-2,6-dinitrobenzenes

Sipyagin, A. M.; Enshov, V. S.; Kashtanov, S. A.; Bateman, Colin P.; Mullen, Brian; Tan, Ying‐Teck; Thrasher, Joseph S.

doi:10.1016/j.jfluchem.2004.03.008

Cited by 45 publications

(25 citation statements)

References 17 publications

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“…A related methodology was used later on for the synthesis of two other nitro-substituted SF 5 benzenes (Yields 29-43%) (Scheme 31) [65].…”

Section: Scheme 30mentioning

confidence: 99%

“…The chlorine atom was shown to be very reactive towards substitution with different nucleophiles that provided good yields of the corresponding nitro-compounds, which were reduced with Fe/HCl to the anilines. An interesting bis-SF 5 -biaryl was also synthesised via Ullman-type coupling (Scheme 86) [65].…”

Section: Scheme 84mentioning

confidence: 99%

“…4-Chloro-3,5-dinitro SF 5 -benzene was submitted as well to nucleophilic substitution reaction with secondary amines affording good yields of the resulting tertiary amines (Scheme 87) [65].…”

Section: Scheme 84mentioning

confidence: 99%

“…In the CF 3 -compound also the nitro moiety was found to be a good leaving group affording the thianthrene via dimerisation of the intermediate aryl xanthate, whereas the SF 5 -compound underwent only loss of COS affording the monomeric ethylthio derivative (Scheme 88) [65].…”

Section: Scheme 84mentioning

confidence: 99%

“…ethyl thiolacetate, provided the expected nucleophilic substitution product which was subjected to intramolecular condensation affording a benzothiazole N-oxide (Scheme 89) [65].…”

Section: Scheme 84mentioning

confidence: 99%

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

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

197

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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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“…A related methodology was used later on for the synthesis of two other nitro-substituted SF 5 benzenes (Yields 29-43%) (Scheme 31) [65].…”

Section: Scheme 30mentioning

confidence: 99%

Section: Scheme 84mentioning

confidence: 99%

Section: Scheme 84mentioning

confidence: 99%

Section: Scheme 84mentioning

confidence: 99%

“…ethyl thiolacetate, provided the expected nucleophilic substitution product which was subjected to intramolecular condensation affording a benzothiazole N-oxide (Scheme 89) [65].…”

Section: Scheme 84mentioning

confidence: 99%

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