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Keywords:

  • deprotonation;
  • inverse crown compounds;
  • magnesium;
  • metalation;
  • sodium
Thumbnail image of graphical abstract

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).