metallocarboxylation

Metallocarboxylation is a type of organometallic reaction where a carbon dioxide molecule is inserted into a metal-carbon bond. This process typically involves an organometallic reagent, such as an organolithium or organomagnesium compound, reacting with carbon dioxide. The general mechanism involves the nucleophilic attack of the carbanionic carbon atom of the organometallic species on the electrophilic carbon atom of carbon dioxide. This insertion forms a metal carboxylate intermediate. Subsequent protonation of this intermediate yields the corresponding carboxylic acid.

This reaction is a fundamental method for synthesizing carboxylic acids and their derivatives. It is widely used in organic synthesis due to the ready availability of both organometallic reagents and carbon dioxide. The reaction conditions can be varied, often involving low temperatures to control reactivity and prevent side reactions. Solvents like diethyl ether or tetrahydrofuran are commonly employed. Variations of metallocarboxylation exist, including those involving transition metals, which can facilitate different reaction pathways or provide access to more complex carboxylated products. The efficiency and scope of metallocarboxylation depend on the nature of the organometallic reagent, the carbon dioxide source, and the reaction conditions. It is a valuable tool for introducing a carboxyl group into organic molecules, enabling the construction of a diverse range of organic compounds.