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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Tri(phosphonio)methanide dication 32+, prepared from a trifluoromethylsulfanylphosphonium dication (12+) via an intramolecular electrophilic aromatic substitution reaction, is an unexpected P-based, water-resistant Lewis acid that is capable to selectively and reversibly bind fluoride ions from organic/aqueous biphasic solution. 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 chemical calculation. Compound [3-F]OTf can also be used as a convenient anhydrous fluoride ion source and was probed as a suitable catalyst of the silylotrifluoromethylation of various aldehydes.
Original languageEnglish
Pages (from-to)7907–7911
JournalAngewandte Chemie - International Edition
Volume56
Issue number27
DOIs
Publication statusPublished - 2017

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