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 language | English |
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Pages (from-to) | 7907–7911 |
Journal | Angewandte Chemie - International Edition |
Volume | 56 |
Issue number | 27 |
DOIs | |
Publication status | Published - 2017 |