Promotional effect of ionic liquids in the electrophilic fluorination of phenols

Promotional effect of ionic liquids in the electrophilic fluorination of phenols Full article

Journal

ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012

Output data

Year: 2018, Pages: 60-71 Pages count : 12 DOI: 10.24820/ark.5550190.p010.164

Tags

Fluorination; phenols; ionic liquid; solvent

Authors

Borodkin Gennady I. ^1,2 , Elanov Innokenty R. ¹ , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Academician Lavrentev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogov St 2, Novosibirsk 630090, Russia

The influence of a stoichiometric amount of ionic liquids (IL) on the fluorination of phenols in various solvents has been studied. The fluorination of phenol, 1-naphthol and resorcinol was carried out using 1-chloromethyl-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4, Selectfluor (TM)) with the formation of 2-fluoro-, 4-fluorophenol, 2-fluoro-, 4-fluoronaphthol and 4-fluoro-, 4,6-difluoro-benzene-l,3-diol as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reactions. The effect is most significant at low temperatures. It has been found that solvent polarity has an essential effect on the difference in yields of fluoroproducts obtained in the presence of IL and without it.

Borodkin G.I. , Elanov I.R. , Shubin V.G.
Promotional effect of ionic liquids in the electrophilic fluorination of phenols

ARKIVOC. 2018. P.60-71. DOI: 10.24820/ark.5550190.p010.164 WOS Scopus РИНЦ

Full text from publisher

Published online:

Oct 15, 2017

Web of science	WOS:000438796300006
Scopus	2-s2.0-85041107864
Elibrary	35536824
OpenAlex	W2771853456