Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides

Iridium-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were investigated by using [IrCl(cod)](2) as catalyst, and dppe was found to be the most suitable phosphine ligand for the reaction. No oxidative insertion of the iridium into the carbon–halide bond was observe...

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Autores principales: Tigchelaar, Andrew, Tam, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511010/
https://www.ncbi.nlm.nih.gov/pubmed/23209510
http://dx.doi.org/10.3762/bjoc.8.201
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author Tigchelaar, Andrew
Tam, William
author_facet Tigchelaar, Andrew
Tam, William
author_sort Tigchelaar, Andrew
collection PubMed
description Iridium-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were investigated by using [IrCl(cod)](2) as catalyst, and dppe was found to be the most suitable phosphine ligand for the reaction. No oxidative insertion of the iridium into the carbon–halide bond was observed, and the reactions proceeded to provide the halogenated cycloadducts in good yield (75–94%). These results are the first examples of cycloadditions of alkynyl halides using an iridium catalyst.
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spelling pubmed-35110102012-12-03 Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides Tigchelaar, Andrew Tam, William Beilstein J Org Chem Full Research Paper Iridium-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were investigated by using [IrCl(cod)](2) as catalyst, and dppe was found to be the most suitable phosphine ligand for the reaction. No oxidative insertion of the iridium into the carbon–halide bond was observed, and the reactions proceeded to provide the halogenated cycloadducts in good yield (75–94%). These results are the first examples of cycloadditions of alkynyl halides using an iridium catalyst. Beilstein-Institut 2012-10-16 /pmc/articles/PMC3511010/ /pubmed/23209510 http://dx.doi.org/10.3762/bjoc.8.201 Text en Copyright © 2012, Tigchelaar and Tam https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tigchelaar, Andrew
Tam, William
Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title_full Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title_fullStr Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title_full_unstemmed Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title_short Iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
title_sort iridium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511010/
https://www.ncbi.nlm.nih.gov/pubmed/23209510
http://dx.doi.org/10.3762/bjoc.8.201
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AT tamwilliam iridiumcatalyzedintramolecular42cycloadditionsofalkynylhalides

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