A metal-free, one-pot method for the oxidative cleavage of internal aliphatic alkenes into carboxylic acids

Abstract

The oxidative cleavage of terpenes and unsaturated fatty acids into carbonyl compounds is an industrially interesting reaction. We have developed a metal-free protocol that can oxidatively cleave unsaturated fatty acids, terpenes and a variety of other alkenes into carboxylic acids in a synthetically straightforward, one-pot protocol. Near stoichiometric amounts of a combination of oxone and periodate are used in aqueous acetonitrile without additional additives, acids or emulsifiers. The solvent system and the reaction temperature have a profound influence on the reactivity of the substrates; conditions have been optimized for a broad scope of alkenes. The products can be isolated by simple extraction with an organic solvent without additional purification: the carboxylic acids are obtained in high yield (80–96%) as colourless solid or liquid products.