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. 2014 Jan 7;53(2):553-6.
doi: 10.1002/anie.201306884. Epub 2013 Nov 24.

Insights into the metalation of benzene and toluene by Schlosser's base: a superbasic cluster comprising PhK, PhLi, and tBuOLi

Christian Unkelbach  1 , Donal F O'Shea, Carsten Strohmann
Affiliations

Insights into the metalation of benzene and toluene by Schlosser's base: a superbasic cluster comprising PhK, PhLi, and tBuOLi

Christian Unkelbach et al. Angew Chem Int Ed Engl. .

Abstract

The metalation of benzene by Schlosser's base (nBuLi/tBuOK) occurs smoothly in THF at low temperatures to afford a discrete mixed-metal Li2 K4 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.

Keywords: alkali metals; carbanions; heterometallic complexes; superbase metalation.

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