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

Yogendra Sivathmeehan | Zendy; Hennersdorf Felix | Zendy; Bauzá Antonio | Zendy; Frontera Antonio | Zendy; Fischer Roland | Zendy; Weigand Jan J. | Zendy

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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.

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