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Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4 : Toward “Dry” Processes. / Zaikin, Pavel A.; Dyan, Ok Ton; Evtushok, Darya V. et al.

In: European Journal of Organic Chemistry, Vol. 2017, No. 17, 03.05.2017, p. 2469-2474.

Research output: Contribution to journal › Article › peer-review

Harvard

Zaikin, PA, Dyan, OT, Evtushok, DV, Usoltsev, AN, Borodkin, GI, Karpova, EV & Shubin, VG 2017, 'Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes', European Journal of Organic Chemistry, vol. 2017, no. 17, pp. 2469-2474. https://doi.org/10.1002/ejoc.201700179

APA

Zaikin, P. A., Dyan, O. T., Evtushok, D. V., Usoltsev, A. N., Borodkin, G. I., Karpova, E. V., & Shubin, V. G. (2017). Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes. European Journal of Organic Chemistry, 2017(17), 2469-2474. https://doi.org/10.1002/ejoc.201700179

Vancouver

Zaikin PA, Dyan OT, Evtushok DV, Usoltsev AN, Borodkin GI, Karpova EV et al. Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes. European Journal of Organic Chemistry. 2017 May 3;2017(17):2469-2474. doi: 10.1002/ejoc.201700179

Author

Zaikin, Pavel A. ; Dyan, Ok Ton ; Evtushok, Darya V. et al. / Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4 : Toward “Dry” Processes. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 17. pp. 2469-2474.

BibTeX

@article{f01b8aa6d72847249ac2d983cc6e22a3,
title = "Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward “Dry” Processes",
abstract = "An effective protocol for the solvent-free fluorination of electron-rich aromatic compounds with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) is described. The protocol allows the easy and efficient isolation of fluorinated products in high yields and purities with low E factors (kgwaste kgproduct –1) by vacuum-sublimation without the use of any solvent. The solid-state fluorination of naphthalen-2-ol was studied by differential thermal analysis, and scanning electron microscopy was used to obtain evidence for the solid-state process. The crucial influence of alkali-metal carbonates on the rate of the solvent-free fluorination of hydroxynaphthalenes and estrone was demonstrated.",
keywords = "Aromatic substitution, Electrophilic substitution, Fluorine, Solid-state reactions, Sustainable chemistry",
author = "Zaikin, {Pavel A.} and Dyan, {Ok Ton} and Evtushok, {Darya V.} and Usoltsev, {Andrey N.} and Borodkin, {Gennady I.} and Karpova, {Elena V.} and Shubin, {Vyacheslav G.}",
year = "2017",
month = may,
day = "3",
doi = "10.1002/ejoc.201700179",
language = "English",
volume = "2017",
pages = "2469--2474",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "17",

}

RIS

TY - JOUR

T1 - Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4

T2 - Toward “Dry” Processes

AU - Zaikin, Pavel A.

AU - Dyan, Ok Ton

AU - Evtushok, Darya V.

AU - Usoltsev, Andrey N.

AU - Borodkin, Gennady I.

AU - Karpova, Elena V.

AU - Shubin, Vyacheslav G.

PY - 2017/5/3

Y1 - 2017/5/3

N2 - An effective protocol for the solvent-free fluorination of electron-rich aromatic compounds with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) is described. The protocol allows the easy and efficient isolation of fluorinated products in high yields and purities with low E factors (kgwaste kgproduct –1) by vacuum-sublimation without the use of any solvent. The solid-state fluorination of naphthalen-2-ol was studied by differential thermal analysis, and scanning electron microscopy was used to obtain evidence for the solid-state process. The crucial influence of alkali-metal carbonates on the rate of the solvent-free fluorination of hydroxynaphthalenes and estrone was demonstrated.

AB - An effective protocol for the solvent-free fluorination of electron-rich aromatic compounds with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) is described. The protocol allows the easy and efficient isolation of fluorinated products in high yields and purities with low E factors (kgwaste kgproduct –1) by vacuum-sublimation without the use of any solvent. The solid-state fluorination of naphthalen-2-ol was studied by differential thermal analysis, and scanning electron microscopy was used to obtain evidence for the solid-state process. The crucial influence of alkali-metal carbonates on the rate of the solvent-free fluorination of hydroxynaphthalenes and estrone was demonstrated.

KW - Aromatic substitution

KW - Electrophilic substitution

KW - Fluorine

KW - Solid-state reactions

KW - Sustainable chemistry

UR - http://www.scopus.com/inward/record.url?scp=85019018583&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201700179

DO - 10.1002/ejoc.201700179

M3 - Article

AN - SCOPUS:85019018583

VL - 2017

SP - 2469

EP - 2474

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 17

ER -

ID: 10192880