Electrochemically\nInduced Synthesis of <i>N</i>‑Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of <i>N</i>‑Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom

The\nelectrochemically induced reaction between alkenes,\nbearing an allylic hydrogen atom, and <i>N</i>-hydroxyphthalimide\nwas investigated. Cross-dehydrogenative C–O coupling with phthalimide-<i>N</i>-oxyl radical, derived from <i>N</i>-hydroxyphthalimide,\noccurs instead of oxidation of the allylic site, with the formation\nof a carbonyl group or functionalization of the double CC\nbond. The discovered transformation proceeds in an undivided electrochemical\ncell equipped with a carbon felt anode and a platinum cathode. Coupling\nproducts were obtained with yields up to 79%. The developed process\nis based on the abstraction of hydrogen atom from the allylic position\nfor functionalization while the CC bond remains unreacted.\nThe method exploits the ability of the phthalimide-<i>N</i>-oxyl radical to abstract hydrogen atoms with the following interception\nof the intermediate <i>C</i>-centered radical.