Improved and facile addition reactions of pentafluorosulfanyl bromide

Lim, Dong Sung; Ngo, Silvana C.; Lal, Sankar G.; Minnich, Kristen E.; Welch, John T.

doi:10.1016/j.tetlet.2008.07.080

Cited by 19 publications

(18 citation statements)

References 8 publications

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“…The facile formation of the desired tetrafluoro-l 6 -sulfanes in good yields is supported by computations suggesting that homolytic cleavage of the S À Cl bond of 3 a requires approximately 6.7 kcal mol À1 less energy than homolytic cleavage of the SÀCl bond of SF 5 Cl (B3LYP/6-31 + G(d,p)). [10] In contrast to the triethylboron-facilitated addition of SF 5 Cl to alkenes and alkynes where a nonpolar solvent such as pentane npentane or trichlorofluoromethane is required to suppress ionic halofluorination, [11] the ease of homolytic S À Cl bond cleavage in 3, presumably a consequence of the reduced electronegativity of aryl tetrafluoro-l 6 -sulfane, enables the use of ethereal solvent.…”

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confidence: 99%

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes

et al. 2013

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Substituted alkenyl aryl tetrafluoro-λ(6) -sulfanes have been prepared by the direct addition of readily accessible chlorotetrafluorosulfanyl arenes to primary alkynes. Substitution of an apical fluorine of the pentafluorosulfanyl group enables modulation of the reactivity of this little explored functional group while at the same time facilitating the direct investigation of aryl substituent effects on the aryl tetrafluorosulfanyl-substituted products.

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Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes

et al. 2013

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“…The aliphatic substituted addition products were more sensitive toward substituent effects than the aromatic-substituted compounds previously communicated. The addition of ethereal solutions of chlorotetrafluorosulfanyl arenes 1 to 1-hexyne 2 and 1-hexene 4 [18] was catalyzed by triethylborane [8,9] (Scheme 1), forming 3 and 5, respectively, in as few as 15 min. The addition reactions could also be initiated photochemically, albeit longer reaction times were required.…”

Section: Resultsmentioning

confidence: 99%

“…Renewed interest in the chemistry of SF 5 -containing compounds accompanied the development of efficient and convenient procedures for pentafluorosulfanylation [5][6][7][8][9][10][11]. Concurrent with these advances, recognition of the stability and potential applications of tetrafluoro-l 6 -sulfanyl-containing materials suggests even more extensive applications of hypervalent fluorinated sulfur compounds [12].…”

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confidence: 99%

Effects of substitution on the reactivity of alkyl aryl tetrafluoro-λ6-sulfanes

Zhong¹,

Filatov²,

Welch³

2014

Journal of Fluorine Chemistry

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“…An important step forward in the synthesis of SF 5 -alkyl compounds was recently achieved by Welch et al who reported that the use of CCl 3 F as a solvent can strongly improve the Et 3 B-catalysed addition of SF 5 Br to C=C bonds, using operatively simple conditions such as normal glassware, ambient pressure and a temperature of 0 °C (Scheme 23 and Table 5) [54]. The use of CCl 3 F as a solvent was then successfully extended to the Et 3 B-catalysed addition of SF 5 Br to various unsaturated esters, which produced the corresponding bromo-pentafluorosulfanylated esters in excellent yields (Scheme 24 and Table 6).…”

Section: Scheme 22mentioning

confidence: 99%

“…The use of CCl 3 F as a solvent was then successfully extended to the Et 3 B-catalysed addition of SF 5 Br to various unsaturated esters, which produced the corresponding bromo-pentafluorosulfanylated esters in excellent yields (Scheme 24 and Table 6). The use of SF 5 Cl afforded lower yields, and addition of DBU resulted in efficient dehydrobromination of the products [54]. Addition of SF 5 Cl to allyl acetate was subsequently described to occur efficiently [55].…”

Section: Scheme 22mentioning

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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Improved and facile addition reactions of pentafluorosulfanyl bromide

Cited by 19 publications

References 8 publications

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes

Effects of substitution on the reactivity of alkyl aryl tetrafluoro-λ6-sulfanes

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

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Improved and facile addition reactions of pentafluorosulfanyl bromide

Cited by 19 publications

References 8 publications

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ6‐sulfanes

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ6‐sulfanes

Effects of substitution on the reactivity of alkyl aryl tetrafluoro-λ6-sulfanes

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

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Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes

Preparation and Characterization of Alkenyl Aryl Tetrafluoro‐λ⁶‐sulfanes