Orthocarboxylated

Orthocarboxylated is a chemical descriptor used to denote a molecule that has one or more carboxylate groups installed at the ortho position relative to a reference site, typically an existing substituent on an aromatic ring or another functional handle. In practice, orthocarboxylation refers to regioselective carbon–carbon bond forming processes that place carboxylate functionalities in the ortho position to a preexisting group, often using directing groups, transition metal catalysis, or carbon dioxide as the C1 source.

The term is commonly encountered in discussions of aromatic C–H functionalization and carboxylation strategies, where the goal is to convert C–H bonds at the ortho position into C–CO2R bonds. This can yield ortho-carboxylated products such as salicylates or o-carboxylated arenes, depending on the substrate and protective groups. Reactions may employ catalytic systems to control regioselectivity and to tolerate various functional groups; some methods also enable subsequent transformations of the carboxylate into esters, acids, or amides.

Orthocarboxylated compounds are of interest in organic synthesis and pharmaceutical chemistry as routes to bioactive scaffolds and as precursors to dyes and polymerizable monomers. Challenges include controlling overcarboxylation, directing group compatibility, and sustainable use of CO2 or other carboxylating agents.

See also: ortho-carboxylation, carboxylation, directed C–H functionalization, salicylates.