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Solvent‐Free Fluorination of Electron‐Rich Aromatic Compounds with F‐TEDA‐BF 4 : Toward “Dry” Processes
Author(s) -
Zaikin Pavel A.,
Dyan Ok Ton,
Evtushok Darya V.,
Usoltsev Andrey N.,
Borodkin Gennady I.,
Karpova Elena V.,
Shubin Vyacheslav G.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700179
Subject(s) - chemistry , sublimation (psychology) , solvent , octane , organic chemistry , halogenation , tetrafluoroborate , inorganic chemistry , ionic liquid , catalysis , psychology , psychotherapist
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‐BF 4 ) 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.