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Issue 13, 2019
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Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation

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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.

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

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Supplementary files

Article information


Submitted
12 Dec 2018
Accepted
18 Feb 2019
First published
19 Feb 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 3802-3806
Article type
Edge Article

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

E. M. D. Allouche and A. B. Charette, Chem. Sci., 2019, 10, 3802
DOI: 10.1039/C8SC05558K

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