Preparation of the first ortho-substituted pentafluorosulfanylbenzenes

Sipyagin, A. M.; Bateman, Colin P.; Tan, Ying‐Teck; Thrasher, Joseph S.

doi:10.1016/s0022-1139(01)00514-0

Cited by 41 publications

(24 citation statements)

References 18 publications

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“…The first ortho-substituted SF 5 -benzene was synthesised by AgF 2 -promoted fluorination of the corresponding disulfide (Scheme 33), although the scope of the reaction seems to be limited because other structurally related substrates did not afford the desired SF 5 -compounds [68]. A few years later, more ortho-fluorinated SF 5 -aryl compounds were obtained in low yields ( 10%) by treatment of a disulfide precursor with F 2 /N 2 [69].…”

Section: Scheme 32mentioning

confidence: 99%

“…A small library of ortho-substituted SF 5 -compounds was obtained starting from 2-fluoro-5-nitro-SF 5 -benzene which is highly activated towards nucleophilic aromatic substitution and was therefore submitted to a range of reactions with different nitrogen-, oxygen-and sulphur-centered nucleophiles such as piperidine, potassium ethylate, ammonia, sodium thiolate affording the corresponding fluoride-substitution products (Scheme 85) [68].…”

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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Section: Scheme 32mentioning

confidence: 99%

Section: Scheme 84mentioning

confidence: 99%

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

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

197

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“…For example, in 1998 worldwide sales of trifluralin were estimated at US$ 300 million with 24,000 metric tons being produced [7,8]. Surprisingly, even with the recent increased interest in superlipophilic groups [9][10][11][12][13], the corresponding SF 5 , CF 3 S, and C 2 F 5 S analogues of trifluralin have not been reported yet.…”

Section: Introductionmentioning

confidence: 99%

“…Another approach would be to synthesize a disulfide that, once fluorinated, contains a halogen that is activated towards nucleophilic aromatic substitution (i.e., ortho or para to the SF 5 group) [20]. Ortho-substituted SF 5 -benzene derivatives [13] are examples of this approach as are the derivatives described herein.…”

Section: Introductionmentioning

confidence: 99%

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

Sipyagin

Enshov

Kashtanov

et al. 2004

Journal of Fluorine Chemistry

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“…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]. We have found that SF 5 Br, when photolysed in benzene, yields SF 5 C 6 H 5 in small quantities [4].…”

Section: Introductionmentioning

confidence: 99%