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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2019
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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. |
format | Online Article Text |
id | pubmed-6457201 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
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title_fullStr | Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
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title_full_unstemmed | Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
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title_short | Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation
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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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