Organometallic chemistry

The chemistry of compounds containing metal–carbon bonds, including their structures, bonding and transformations in stoichiometric and catalytic reactions.

Metalation introduces a metal into a molecule or replaces an attached atom or group with a metal-containing connection. In organometallic chemistry, the term often refers to forming a carbon–metal chemical bond, for example by replacing a carbon-bound hydrogen.

The word describes the transformation, while the mechanism can involve proton transfer, metal insertion or other pathways. A metalated carbon centre may act as a nucleophile in a subsequent bond-forming reaction. Which site is metalated depends on acidity, coordination and kinetics, so the most acidic isolated bond need not uniquely predict the product under every reaction condition.

Cleavage of a carbon–carbon bond beta to a metal, often from a metal alkoxide, coupled to carbonyl formation and transfer of a carbon fragment to the metal. For a tertiary benzylic alkoxide this can generate a ketone and a metal–aryl bond.