Influence of sulfonyl substituents on the decomposition of N -sulfonylhydrazones at room temperature

A detailed study of the dissociation performance of structurally varied N -sulfonylhydrazones was described, and N -tfsylhydrazone was proved to be the best substrate to give the corresponding diazo compound at room temperature. N -Tfsylhydrazone is capable of releasing nonstabilized aryldiazomethane in a wide range of solvents in the presence of various commonly used bases under mild reaction conditions (−25 °C to 40 °C). The utility of the strategy is established by late-stage derivatization of bioactive molecules and several typically sensitive reactions, in which highly purified diazo compounds are required.