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Trifluoromethylboranes and ‐Borates: New Synthetic Strategies and Applications
Author(s) -
Finze Maik,
Bernhardt Eduard,
Willner Helge
Publication year - 2007
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.200700826
Subject(s) - borane , chemistry , nucleophile , ligand (biochemistry) , lewis acids and bases , medicinal chemistry , boranes , anhydrous , superacid , boron , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
The synthesis of salts with the [B(CF 3 ) 4 ] − anion has been the starting point for new developments in the field of trifluoromethylboron chemistry. In contrast to the previous syntheses of (CF 3 ) n B derivatives (n=1–3), achieved exclusively by CF 3 transfer, the synthesis of the [B(CF 3 ) 4 ] − anion was accomplished by fluorination of the [B(CN) 4 ] − anion with ClF or ClF 3 in anhydrous HF. Owing to its thermal and chemical stability, [B(CF 3 ) 4 ] − is an attractive weakly coordinating anion. However, in concentrated sulfuric acid one of the four CF 3 groups is solvolyzed to a CO ligand to yield the neutral borane carbonyl (CF 3 ) 3 BCO. It has been shown that the borane carbonyl compound is a versatile synthetic building block, and numerous reactions have been investigated. The addition of nucleophiles to the C atom of the CO ligand is favored, and examples for new derivatives are the anions [(CF 3 ) 3 BCPnic] − (Pnic=N, P, As). Under certain conditions, ligand‐exchange reactions are also observed, for example, the formation of (CF 3 ) 3 BNCH. Finally, the borane carbonyl compound is a component of the conjugated Brønsted–Lewis superacid HF/(CF 3 ) 3 BCO.