Insights into the Metalation of Benzene and Toluene by Schlosser’s Base: A Superbasic Cluster Comprising PhK, PhLi, and  t BuOLi | Zendy

Unkelbach Christian | Zendy; O'Shea Donal F. | Zendy; Strohmann Carsten | Zendy

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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.

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