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Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward "Dry" Processes Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2017, Volume: 2017, Number: 17, Pages: 2469-2474 Pages count : 6 DOI: 10.1002/ejoc.201700179
Tags Aromatic substitution; Electrophilic substitution; Fluorine; Solid-state reactions; Sustainable chemistry
Authors Zaikin Pavel A. 1 , Dyan Ok Ton 1 , Evtushok Darya V. 3 , Usoltsev Andrey N. 3 , Borodkin Gennady I. 1,2 , Karpova Elena V. 1,2 , Shubin Vyacheslav G. 1
Affiliations
1 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Acad Lavrentiev Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, 2 Pirogov St, Novosibirsk, Russia
3 (Данные Web of science) Russian Acad Sci, AV Nikolaev Inst Inorgan Chem, Siberian Branch, 3 Acad Lavrentiev Ave, Novosibirsk 630090, Russia

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 (kg(waste)kg(product)(-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.
Cite: Zaikin P.A. , Dyan O.T. , Evtushok D.V. , Usoltsev A.N. , Borodkin G.I. , Karpova E.V. , Shubin V.G.
Solvent-Free Fluorination of Electron-Rich Aromatic Compounds with F-TEDA-BF4: Toward "Dry" Processes
European Journal of Organic Chemistry. 2017. V.2017. N17. P.2469-2474. DOI: 10.1002/ejoc.201700179 WOS Scopus РИНЦ
Dates:
Published print: May 3, 2017
Published online: May 3, 2017
Identifiers:
Web of science WOS:000400993800010
Scopus 2-s2.0-85019018583
Elibrary 31038665
OpenAlex W2593233388
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