Selective and Reversible Fluoride Complexation from Water by a Cyclic Tri(phosphonio)methanide Dication.

Sivathmeehan Yogendra, Felix Hennersdorf, Antonio Bauza, Antonio Frontera, Roland Fischer, Jan J. Weigand

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Tri(phosphonio)methanide dication 32+, prepd. from a trifluoromethylsulfanylphosphonium dication (12+) via an intramol. electrophilic arom. substitution reaction, is an unexpected P-based, water-resistant Lewis acid that is capable to selectively and reversibly bind fluoride ions from org./aq. biphasic soln. The formed complex is an unusual fluorophosphorane ([3-F]OTf). The multiple donor-acceptor interactions of 32+ that are crucial for the fluoride fixation have been elucidated by quantum chem. calcn. Compd. [3-F]OTf can also be used as a convenient anhyd. fluoride ion source and was probed as a suitable catalyst of the silylotrifluoromethylation of various aldehydes. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)7907–7911
JournalAngewandte Chemie / International Edition
Issue number27
Publication statusPublished - 2017

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