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Wiley, Angewandte Chemie, 27(129), p. 8015-8019

DOI: 10.1002/ange.201701570

Wiley, Angewandte Chemie International Edition, 27(56), p. 7907-7911

DOI: 10.1002/anie.201701570

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

Journal article published in 2017 by Sivathmeehan Yogendra ORCID, Felix Hennersdorf, Antonio Bauzá, Antonio Frontera, Roland Fischer, Jan J. Weigand ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

AbstractTri(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.