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Chemistry for Sustainable Development

2011 year, number 6

Eco-Friendly Fluorination of Aromatic Compounds with F-TEDA-BF4 Reagent in Water

G. I. BORODKIN,В В P. A. ZAIKINВ В andВ В V. G. SHUBIN
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
Pr. Akademika Lavrentyeva 9, Novosibirsk 630090 (Russia)
gibor@nioch.nsc.ru
Keywords: NF reagent, electrophilic fluorination, selectivity, eco-friendly solvents, water, phenols, acetanilide and heteroaromatic compounds
Pages: 593–598

Abstract

The interaction of bis(tetrafluoroborate) of 1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane (F-TEDA-BF4) with phenol, acetanilide and their derivatives, resorcinol, 1-, 2-naphthols and 6-methoxyquinoline in water was investigated. In some cases, fluorination of aromatic compounds in water proceeds more selectively than in the case when organic solvents are used.

UDC 544.164.032.6