Electrochemical Synthesis of O‐Phthalimide Oximes from α‐Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide‐N‐Oxyl and Iminyl Radicals with C−O/N−O Bonds Formation

Abstract Electrochemically induced radical‐initiated reaction of vinyl azides with N ‐hydroxyphthalimide resulting O ‐phthalimide oximes with challenging for organic chemistry N−O‐N fragment has been discovered. The developed approach introduces in synthesis electrochemically generated O‐centered imide‐ N ‐oxyl radicals as the coupling components. Sequential formation of C−O and N−O bonds was achieved via generation and selective addition of imide‐ N ‐oxyl radicals, followed by recombination with iminyl radicals. A wide range of O ‐phthalimide oximes was obtained with the yields up to 84%. magnified image