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Insights into the Metalation of Benzene and Toluene by Schlosser’s Base: A Superbasic Cluster Comprising PhK, PhLi, and t BuOLi
Author(s) -
Unkelbach Christian,
O'Shea Donal F.,
Strohmann Carsten
Publication year - 2014
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.201306884
Subject(s) - toluene , metalation , delocalized electron , benzene , chemistry , cluster (spacecraft) , counterion , medicinal chemistry , base (topology) , polymer chemistry , ion , organic chemistry , mathematics , computer science , programming language , mathematical analysis
The metalation of benzene by Schlosser’s base ( n BuLi/ t BuOK) occurs smoothly in THF at low temperatures to afford a discrete mixed‐metal Li 2 K 4 cluster that contains phenyl anions and tert ‐butoxide. The aggregate itself exhibits superbasic behavior by metalating toluene. The delocalized benzyl anion obtained this way π bonds to potassium counterions, thereby creating a 2D coordination polymer.