Premium
Selective Meta ‐Deprotonation of Toluene by Using Alkali‐Metal‐Mediated Magnesiation
Author(s) -
Andrikopoulos Prokopis C.,
Armstrong David R.,
Graham David V.,
Hevia Eva,
Kennedy Alan R.,
Mulvey Robert E.,
O'Hara Charles T.,
Talmard Christine
Publication year - 2005
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.200500379
Subject(s) - deprotonation , metalation , toluene , bimetallic strip , chemistry , alkali metal , ring (chemistry) , medicinal chemistry , metal , inorganic chemistry , organic chemistry , ion
Back to bases : Conventional organometallic bases usually deprotonate toluene at the methyl position to generate resonance‐stabilized benzyl anions, but using a new type of bimetallic metalation, sodium‐mediated magnesiation, the thermodynamic position for deprotonation can be switched to the aromatic ring (see picture).