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Main group organometallic reagents in organic synthesis, ST

Preparation

Insertion

In the insertion (reduction) method of preparing a main group organometallic reagent, a metallic main group element M reacts with an organohalide RX. The term reduction refers to the fact that the oxidation state of carbon in the organohalide decreases by two units. For example, MeClMeLi can be thought of as carbon(+1) → carbon(−1), or [H3C+ Cl] → [H3C Li+]. In reality, MeCl and MeLi are much more covalent than this ionic formulation, but it highlights the change in formal oxidation state.

  • Halogen remains in the −1 oxidation state throughout
  • Oxidation state of carbon decreases by two units
  • Oxidation state of metal increases by two units (or two metals atoms are both oxidised by one unit): M → M2+ + 2e or two lots of M → M+ + e
  • For a Group 1 metal: RX + 2M0 → RMI + MIX
  • For a Group 2 metal: RX + M0 → RMIIX