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CF Activation of Fluorobenzene by Silylium Carboranes: Evidence for Incipient Phenyl Cation Reactivity
Author(s) -
Duttwyler Simon,
Douvris Christos,
Fackler Nathanael L. P.,
Tham Fook S.,
Reed Christopher A.,
Baldridge Kim K.,
Siegel Jay S.
Publication year - 2010
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.201003762
Subject(s) - fluorobenzene , reactivity (psychology) , chemistry , fluoride , silylation , medicinal chemistry , lewis acids and bases , ion , inorganic chemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology , benzene
Si(mply) rips it apart : CF activation of fluorobenzene has been achieved using the extremely strong silyl Lewis acids [Et 3 Si(X)] + (X=PhF or Et 3 SiH) and [(2,6‐dixylyl‐C 6 H 3 )SiMe 2 ] + paired with the anion CHB 11 Cl 11 − . They abstract fluoride from unactivated fluorobenzene to give arylated products, consistent with phenyl‐cation‐like reactivity (see scheme).