Structure-reactivity relationships of N-hydroxysaccharin analogues as organocatalysts for aerobic oxidation

Abstract The structure-reactivity relationships of new N -hydroxysaccharin analogous organocatalysts for aerobic oxidation have been theoretically explored based on the replacements of carbonyl groups in the succinimide ring of N -hydroxyphthalimide and N , N -dihydroxypyromellitimide by sulfinyl or sulfonyl groups. Both sulfinyl and sulfonyl groups largely change catalytic reactivity by altering the planar resonance/conjugation structures of precursors. Sulfinyl group largely decreases the reactivity, and the reactivity of catalyst with single sulfonyl group in the succinimide ring is higher than that with double sulfonyl groups. The reactivity of multi-nitroxyl catalysts is higher than that of the corresponding mono-cases, which is even comparable to that of N , N -dihydroxypyromellitimide.