Alkanedioic Acids and Derivatives

This review presents strategies for the synthesis of alkanedioic acids that have been published since the previous Science of Synthesis article on this topic, and covers methods reported since around 2007. Some examples of the formation of the corresponding diesters and other derivatives are also included. Carbon monoxide (CO) and carbon dioxide (CO₂) are fundamental C₁ resources, and as such their utilization to prepare carboxylic acid derivatives has gained increasing attention. Transition-metal-catalyzed hydrocarbonylation of unsaturated carbon–carbon bonds constitutes a straightforward approach to carboxylic acid derivatives. When a diene or alkyne is used as the starting material, double hydrocarbonylation would directly deliver the desired alkanedioic acids or esters. In particular, chiral variants of substituted succinic acids and esters can be readily prepared by asymmetric hydrocarbonylation. During the last decade, electrochemical carboxylation of alkenes to produce carboxylic acids has also been explored. Double electrocarboxylation, incorporating two molecules of carbon dioxide to one molecule of alkene, could efficiently prepare the alkanedioic acids in one step.