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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,  P. A. ZAIKIN  and  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