An alternative picture of alkali-metal-mediated metallation: cleave and capture chemistry

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Abstract

This perspective article takes an alternative look at alkali-metal-mediated chemistry (exchange of a relatively inert C-H bond for a more reactive C-metal bond by a multicomponent reagent usually containing an alkali metal and a less electropositive metal such as magnesium or zinc). It pictures that the cleavage of selected C-H bonds can be accompanied by the capturing of the generated anion by the multi (Lewis acid)-(Lewis base) character of the residue of the bimetallic base. In this way small atoms or molecules (hydrides, oxygen-based anions) as well as sensitive organic anions (of substituted aromatic compounds, ethers or alkenes) can be captured. Cleave and capture reactions which occur in special positions on the organic substrate are also included.

Original languageEnglish
Pages (from-to)6676-6693
Number of pages18
JournalDalton Transactions
Volume42
Issue number19
Early online date18 Feb 2013
DOIs
Publication statusPublished - 2013

Keywords

  • alkali-metal-mediated metallation
  • alkyl
  • magnesium hydride
  • functionalized aromatics
  • aluminium compounds
  • hydrogen storage
  • structural basis
  • ortho-zincation
  • lithium
  • base
  • ethers
  • cleave and capture chemistry

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