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Selective Meta-Deprotonation of Toluene by Using Alkali-Metal-Mediated Magnesiation


  • This work was supported by the U.K. EPSRC through grant award no. GR/R81183/01, the E.U. through a Marie Curie Fellowship to E.H., and the Royal Society/Leverhulme Trust through a Fellowship to R.E.M.


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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).