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Transformations of Organic Molecules with F-TEDA-BF4 in Ionic Liquid Media
Department of Physical and Organic Chemistry, ‘Jožef Stefan’ Institute, Jamova 39, 1000 Ljubljana, Slovenia
Faculty for Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
* Author to whom correspondence should be addressed.
Received: 11 May 2009; in revised form: 10 June 2009 / Accepted: 3 July 2009 / Published: 6 July 2009
Abstract: The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl-imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.
Keywords: F-TEDA-BF4; fluorination; ionic liquids; green chemistry
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Pavlinac, J.; Zupan, M.; Stavber, S. Transformations of Organic Molecules with F-TEDA-BF4 in Ionic Liquid Media. Molecules 2009, 14, 2394-2409.
Pavlinac J, Zupan M, Stavber S. Transformations of Organic Molecules with F-TEDA-BF4 in Ionic Liquid Media. Molecules. 2009; 14(7):2394-2409.
Pavlinac, Jasminka; Zupan, Marko; Stavber, Stojan. 2009. "Transformations of Organic Molecules with F-TEDA-BF4 in Ionic Liquid Media." Molecules 14, no. 7: 2394-2409.