The reactions of 3,7-dimethylenebicyclo[3.3.1]nonane, norbornadiene and cis,cis-1,5-cyclooctadiene with pentafluoro-λ6-sulfanyl chloride

Ponomarenko, Maxim V.; Serguchev, Yurii A.; Röschenthaler, Gerd‐Volker

doi:10.1016/j.jfluchem.2009.11.021

Cited by 19 publications

(6 citation statements)

References 45 publications

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“…Notably, a chlorination product from nhexane was also detected in the reaction mixture, which supports the formation of hexyl radical. On the basis of the above results and previous reports, [5,20] a plausible reaction mechanism for hydropentafluorosulfanylation of diazo compounds was proposed in Scheme 5 d. Initially, SF 5 radical is generated from SF 5 Cl by the reaction with diazo compounds 1 [25] or photo-irradiation. Then, the addition of SF 5 radical to diazo compounds 1 gives radical intermediate A, which releases of one molecule of N 2 to afford radical intermediate B.…”

mentioning

confidence: 57%

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Shou

Qing

2021

Angew Chem Int Ed

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Pentafluorosulfanyl chloride (SF 5 Cl) is the most prevalent reagent for the incorporation of SF 5 group into organic compounds. However, the preparation of SF 5 Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF 5 Cl in nhexane under gas-reagent-free conditions. The synthetic application of SF 5 Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydroand chloropentafluorosulfanylations of a-diazo carbonyl compounds were developed in the presence of K 3 PO 4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various a-pentafluorosulfanyl carbonyl compounds of high value for potential applications.Scheme 1. Preparation of a solution of SF 5 Cl in n-hexane.

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confidence: 57%

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Shou

Qing

2021

Angew Chem Int Ed

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“…Use of triethylborane as radical initiator improved slightly the yield, but no transannulation was observed (eq 17). 22 The addition of SF5Cl to benzobarralene followed by a sequence of base-promoted HCl elimination / naphthalene formation gave access to 2-pentafluorosulfanylnaphthalene (eq 18). 23 A route to pentafluorosulfanylbenzene (C6H5SF5) was developed through addition of SF5Cl to cyclohexene, followed by HCl elimination, dibromination with N-bromosuccinimide and dehydrobromination under basic conditions to afford the desired C6H5SF5 in 68% overall yield (eq 19).…”

Section: Reactions With C=c Bondsmentioning

confidence: 99%

Pentafluorosulfanyl Chloride

Bizet¹,

Cahard²

2020

Encyclopedia of Reagents for Organic Synthesis

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“…3:1 ratio. Finally, cycloocta-1,5-diene failed to produce transannulation, affording the product arising from simple addition of SF 5 Cl to one of the C=C bonds, in rather modest yields (Scheme 26) [57].…”

Section: Scheme 25mentioning

confidence: 99%

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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The reactions of 3,7-dimethylenebicyclo[3.3.1]nonane, norbornadiene and cis,cis-1,5-cyclooctadiene with pentafluoro-λ6-sulfanyl chloride

Cited by 19 publications

References 45 publications

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Pentafluorosulfanyl Chloride

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

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