Oxidative fluorination of S, Se and Te compounds

Ou, Xiaobo; Janzen, A. F.

doi:10.1016/s0022-1139(99)00171-2

Cited by 49 publications

(49 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[30] Scheme 3. ArSeF 3 : The complete 77 Se and 19 F NMR spectra of arylselenium trifluorides are described here for the first time; for earlier syntheses of RSeF 3 see references [9,24,[31][32][33][34][35]. The NMR data of 5 b, 2 b, 4 b, 6 b, and 9 b are in agreement with a pseudo-trigonal-bipyramidal structure for the selenium center, similar to that in SeF 4 .…”

supporting

confidence: 54%

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

Poleschner

Seppelt

2004

Chemistry A European J

View full text Add to dashboard Cite

Arylselenenyl fluorides ArSeF are obtained from diselenides Ar2Se2 or arylselenotrimethylsilanes ArSe-SiMe3, and XeF2. They are detected by low-temperature 19F and 77Se NMR spectroscopy. Substitution in the ortho position of the aromatic ring to provide electronic or steric protection is a requirement for their formation. ArSe--F compounds decompose according to 3 ArSe-F-->[ArSe-SeF2Ar]+ArSe-F-->ArSeF3+Ar2Se2. Reaction energies for this disproportionation as well as that of the sulfur and tellurium homologues have been calculated with MP2, CCSD(T,) and B3 LYP methods. They were found to be increasingly exothermic in the sequence S

show abstract

supporting

confidence: 54%

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

Poleschner

Seppelt

2004

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The same transformation was achieved 40 years later by using XeF 2 as fluorinating agent (up to 25% yield) [63].…”

Section: Scheme 29mentioning

confidence: 55%

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

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

197

View full text Add to dashboard Cite

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.

show abstract

“…Obwohl SF 5 häufig durch seine Größe, höhere Elektronegativität, bessere hydrolytische Stabilität und größere Lipophilizität als “Super‐Trifluormethyl”‐Gruppe angesehen wird, ist die SF 5 ‐Gruppe und ihre Einsetzbarkeit signifikant weniger erforscht als die CF 3 ‐, OCF 3 ‐ oder SCF 3 ‐Gruppen, was zuallererst dem Problem der synthetischen Zugänglichkeit zuzuschreiben ist. Dies wird verdeutlicht, wenn man sich die langsame Entwicklung der “Aryl‐SF 5 ”‐Chemie über die letzten 60 Jahre vor Augen führt (Abbildung ) …”

Section: Figureunclassified

“… Die langsame Entwicklung der synthetischen Methoden für die Synthese von Aryl‐SF 5 ‐Verbindungen aus Diaryldisulfid‐Substraten und die Evaluation des TCICA/KF‐Ansatzes für die Herstellung von Aryl‐SF 4 Cl‐Schlüsselintermediaten.…”

Section: Figureunclassified

Die SF₅‐Gruppe zugänglicher gemacht: Eine gasfreie Synthese von Aryl‐Tetrafluor‐λ⁶‐Sulfanyl‐Chloriden

Pitts¹,

Bornemann²,

Liebing³

et al. 2019

Angewandte Chemie

View full text Add to dashboard Cite

Moderne Pentafluorosulfanyl(SF5)‐Chemie hat eine entscheidende Schwachstelle: synthetische Zugänglichkeit. In dieser Arbeit präsentieren wir die erste Methode für die Herstellung von Aryl‐SF4Cl‐Verbindungen (Schlüsselintermediate für die Aryl‐SF5‐Synthese), die durch Einsatz von einfach zu handhabender Trichlorisocyanursäure, Kaliumfluorid und katalytischer Mengen an Säure, ohne die Verwendung von gefährlichen Fluorierungsmitteln und oder Gasen als Reaktanden, auskommt. Diese simplen, milden Bedingungen erlauben den direkten Zugang zu Aryl‐SF4Cl‐Intermediaten die mit bisherigen Methoden entweder noch nicht synthetisiert wurden oder nicht synthetisiert werden konnten. Des Weiteren eröffnet diese Methode den Zugang zu Aryl‐SF3‐ und Aryl‐SeF3‐Verbindungen, was die Anwendung dieser Chemie über die Grenzen der SF5‐Funktionalisierung hinaus erweitert und somit eine Lösung zum komplexen Problem der oxidativen Fluorierung anbietet.

show abstract

Oxidative fluorination of S, Se and Te compounds

Cited by 49 publications

References 22 publications

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

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

Die SF₅‐Gruppe zugänglicher gemacht: Eine gasfreie Synthese von Aryl‐Tetrafluor‐λ⁶‐Sulfanyl‐Chloriden

Contact Info

Product

Resources

About

Oxidative fluorination of S, Se and Te compounds

Cited by 49 publications

References 22 publications

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar2Se2/XeF2 and ArSeSiMe3/XeF2 Reagents

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar2Se2/XeF2 and ArSeSiMe3/XeF2 Reagents

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

Die SF5‐Gruppe zugänglicher gemacht: Eine gasfreie Synthese von Aryl‐Tetrafluor‐λ6‐Sulfanyl‐Chloriden

Contact Info

Product

Resources

About

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

First Detection of a Selenenyl Fluoride ArSeF by NMR Spectroscopy: The Nature of Ar₂Se₂/XeF₂ and ArSeSiMe₃/XeF₂ Reagents

Die SF₅‐Gruppe zugänglicher gemacht: Eine gasfreie Synthese von Aryl‐Tetrafluor‐λ⁶‐Sulfanyl‐Chloriden