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Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation.

ABSTRACT: Electron-rich alkyl diazo compounds are powerful reagents in organic synthesis, but the risks associated with their toxicity and instability often limit their uses. Herein we describe an efficient, easy-to-handle and safe batch protocol for the in situ generation and cyclopropanation of these highly reactive non-stabilized diazoalkanes through the oxidation of free hydrazones using iodosylbenzene. Numerous substituted cyclopropanes have been synthesized using this methodology, including various gem-dimethylcyclopropanes of particular interest in medicinal chemistry.

SUBMITTER: Allouche EMD

PROVIDER: S-EPMC6457201 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation.

Allouche Emmanuelle M D EMD Charette André B AB

Chemical science 20190219 13

Electron-rich alkyl diazo compounds are powerful reagents in organic synthesis, but the risks associated with their toxicity and instability often limit their uses. Herein we describe an efficient, easy-to-handle and safe batch protocol for the in situ generation and cyclopropanation of these highly reactive non-stabilized diazoalkanes through the oxidation of free hydrazones using iodosylbenzene. Numerous substituted cyclopropanes have been synthesized using this methodology, including v ...[more]

PMID: 31015921

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