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

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...

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Autores principales: Allouche, Emmanuelle M. D., Charette, André B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6457201/
https://www.ncbi.nlm.nih.gov/pubmed/31015921
http://dx.doi.org/10.1039/c8sc05558k
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author Allouche, Emmanuelle M. D.
Charette, André B.
author_facet Allouche, Emmanuelle M. D.
Charette, André B.
author_sort Allouche, Emmanuelle M. D.
collection PubMed
description 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.
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spelling pubmed-64572012019-04-23 Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation Allouche, Emmanuelle M. D. Charette, André B. Chem Sci Chemistry 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. Royal Society of Chemistry 2019-02-19 /pmc/articles/PMC6457201/ /pubmed/31015921 http://dx.doi.org/10.1039/c8sc05558k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Allouche, Emmanuelle M. D.
Charette, André B.
Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title_full Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title_fullStr Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title_full_unstemmed Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title_short Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
title_sort non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ mirc cyclopropanation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6457201/
https://www.ncbi.nlm.nih.gov/pubmed/31015921
http://dx.doi.org/10.1039/c8sc05558k
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