Electron-rich diazo compounds such as alkyl- and dialkyl- substituted diazomethanes are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their uses. In this presentation, a continuous flow synthesis to access the most reactive non-stabilized diazoalkanes will be discussed as well as applications in novel cyclopropanation reactions.<br/><br/>A safe, easy-to-handle and efficient production of unstable diazo reagents by oxidation of free hydrazones is described, affording an output stream of pure, base- and metal- free diazo solution in dichloromethane. Our efforts to develop greener and recoverable oxidants will also be discussed in this presentation. Moreover, these highly reactive non-stabilized diazoalkanes have been directly used in many subsequent transformations, therefore avoiding accumulation and handling of such dangerous substances.<br/>

Continous flow preparation of non-stabilized diazoalkanes and application to the synthesis of polysubstituted cyclopropane derivatives

256th National Meeting (2018)

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