A safe and user-friendly one-pot process for an iron-catalyzed cyclopropanation reaction of alkenes is described. In this work, N-arylsulfonylhydrazones were screened in order to generate diazo compounds in-situ and in mild conditions, therefore allowing the one-pot generation and degradation of the diazo by the iron catalyst as well as the subsequent cyclopropanation. Various hydrazones and alkenes were successfully submitted to the optimized conditions, allowing the modular synthesis of a wide variety of 1,2-disubstituted cyclopropanes – scaffolds present in numerous bioactive molecules – in good to excellent yields without the need to manipulate hazardous diazo reagents.

Iron-catalyzed synthesis of cyclopropanes by <i>in-situ</i> generation and decomposition of electron-rich diazo compounds

255th National Meeting (2018)

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Iron-catalyzed synthesis of cyclopropanes by in-situ generation and decomposition of electron-rich diazo compounds