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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene / chemistry*
  • Furans / chemistry
  • Lithium / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Potassium / chemistry*
  • Toluene / chemistry*
  • tert-Butyl Alcohol / chemistry*

Substances

  • Furans
  • Organometallic Compounds
  • Toluene
  • tetrahydrofuran
  • Lithium
  • Benzene
  • tert-Butyl Alcohol
  • Potassium