Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C-O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom

The electrochemically induced reaction between alkenes, bearing an allylic hydrogen atom, and N-hydroxyphthalimide was investigated. Cross-dehydrogenative C-O coupling with phthalimide-N-oxyl radical, derived from N-hydroxyphthalimide, occurs instead of oxidation of the allylic site, with the formation of a carbonyl group or functionalization of the double C=C bond. The discovered transformation proceeds in an undivided electrochemical cell equipped with a carbon felt anode and a platinum cathode. Coupling products were obtained with yields up to 79%. The developed process is based on the abstraction of hydrogen atom from the allylic position for functionalization while the C=C bond remains unreacted. The method exploits the ability of the phthalimide-N-oxyl radical to abstract hydrogen atoms with the following interception of the intermediate C-centered radical.