Catalytic and Significant Stoichiometric Use of Sodium Species in Molecular Organic Synthesis

The catalytic and significant stoichiometric use of sodium species as a single metal mediator in molecular organic synthesis has been reviewed. Specific sodium compounds have been identified as: a Lewis acid catalyst; a critical component of a Brønsted acid catalyst; a critical component of a Lewis base or Brønsted base catalyst; electron-rich sodium species may also potentially trigger the formation of radical intermediates. In certain cases, (chiral) sodium compounds have been shown to be a pre-catalyst in (asymmetric) phase-transfer catalysis. Finally, sodium species have proved to display increased reactivity and/or selectivity in the catalysis facilitated by another metal compound (via modification of the catalyst structure and/or anion metathesis).