Oxidative coupling of N-hydroxyphthalimide with toluene

Article abstract of DOI:10.1134/S1070363214110061

Oxidative C-O-coupling of N-hydroxyphthalimide (NHPI) with toluene was studied. The reaction occurred in different organic solvents with a wide range of oxidants, such as (NH₄)₂Ce(NO₃)₆, PhI(OAc)₂, KMnO₄, Mn(OAc)₃·2H₂O, Pb(OAc)₄, and Co(OAc)₂/O₂, to afford N-benzyloxyphthalimide in yield of 11-75%. Phthalimide-N-oxyl radicals, generated under the reaction conditions, could eliminate the hydrogen atom from the benzyl fragment of alkylarene at room temperature. Probably, formation of the product of the oxidative coupling occurred via recombination of benzyl and phthalimide-N-oxyl radicals.