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Selective and Reversible Fluoride Complexation from Water by a Cyclic Tri(phosphonio)methanide Dication
Author(s) -
Yogendra Sivathmeehan,
Hennersdorf Felix,
Bauzá Antonio,
Frontera Antonio,
Fischer Roland,
Weigand Jan J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701570
Subject(s) - dication , fluoride , anhydrous , chemistry , aqueous solution , intramolecular force , electrophile , lewis acids and bases , ion , medicinal chemistry , catalysis , inorganic chemistry , photochemistry , stereochemistry , organic chemistry
Tri(phosphonio)methanide dication 3 2+ , prepared from a trifluoromethylsulfanylphosphonium dication ( 1 2+ ) 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 3 2+ 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.