Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones

The radical azidoalkylation of alkenes that was initially developed with α-iodoesters and α-iodoketones was extended to other activated iodomethyl derivatives. By using iodomethyl aryl sulfones, the preparation of γ-azidosulfones was easily achieved. Facile conversion of these azidosulfones to homoa...

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Detalles Bibliográficos
Autores principales: Millius, Nicolas, Lapointe, Guillaume, Renaud, Philippe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891591/
https://www.ncbi.nlm.nih.gov/pubmed/31752245
http://dx.doi.org/10.3390/molecules24224184
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author Millius, Nicolas
Lapointe, Guillaume
Renaud, Philippe
author_facet Millius, Nicolas
Lapointe, Guillaume
Renaud, Philippe
author_sort Millius, Nicolas
collection PubMed
description The radical azidoalkylation of alkenes that was initially developed with α-iodoesters and α-iodoketones was extended to other activated iodomethyl derivatives. By using iodomethyl aryl sulfones, the preparation of γ-azidosulfones was easily achieved. Facile conversion of these azidosulfones to homoallylic azides using a Julia–Kocienski olefination reaction is reported, making the whole process equivalent to the azidoalkenylation of terminal alkenes.
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spelling pubmed-68915912019-12-12 Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones Millius, Nicolas Lapointe, Guillaume Renaud, Philippe Molecules Article The radical azidoalkylation of alkenes that was initially developed with α-iodoesters and α-iodoketones was extended to other activated iodomethyl derivatives. By using iodomethyl aryl sulfones, the preparation of γ-azidosulfones was easily achieved. Facile conversion of these azidosulfones to homoallylic azides using a Julia–Kocienski olefination reaction is reported, making the whole process equivalent to the azidoalkenylation of terminal alkenes. MDPI 2019-11-18 /pmc/articles/PMC6891591/ /pubmed/31752245 http://dx.doi.org/10.3390/molecules24224184 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Millius, Nicolas
Lapointe, Guillaume
Renaud, Philippe
Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title_full Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title_fullStr Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title_full_unstemmed Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title_short Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones
title_sort two-step azidoalkenylation of terminal alkenes using iodomethyl sulfones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891591/
https://www.ncbi.nlm.nih.gov/pubmed/31752245
http://dx.doi.org/10.3390/molecules24224184
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