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

ABSTRACT: 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 rad

SUBMITTER: Paveliev SA 

PROVIDER: S-EPMC11656238 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature