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A Boronium Ion with Exceptional Electrophilicity
Author(s) -
Prokofjevs Aleksandrs,
Kampf Jeff W.,
Vedejs Edwin
Publication year - 2011
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.201005663
Subject(s) - triethylamine , denticity , steric effects , electrophile , chemistry , adduct , stereochemistry , medicinal chemistry , organic chemistry , crystal structure , catalysis
Barely bidentate : The adduct of dimethylamino naphthalene (proton sponge) and 9‐BBN‐NTf 2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9‐BBN‐NEt 3 + Tf 2 N − ) lacking any n‐ or π‐donor substitutents.