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Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**

The regioselective conversion of propargylic alcohols into previously unreported α,α-diiodo-β-hydroxyketones was achieved by treatment with N-iodosuccinimide in the presence of a gold catalyst. The corresponding α,α-dichloro-β-hydroxyketones were obtained by treatment with trichloroisocyanuric acid...

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Autores principales: D’Oyley, Jarryl M, Aliev, Abil E, Sheppard, Tom D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4271674/
https://www.ncbi.nlm.nih.gov/pubmed/25147077
http://dx.doi.org/10.1002/anie.201405348
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author D’Oyley, Jarryl M
Aliev, Abil E
Sheppard, Tom D
author_facet D’Oyley, Jarryl M
Aliev, Abil E
Sheppard, Tom D
author_sort D’Oyley, Jarryl M
collection PubMed
description The regioselective conversion of propargylic alcohols into previously unreported α,α-diiodo-β-hydroxyketones was achieved by treatment with N-iodosuccinimide in the presence of a gold catalyst. The corresponding α,α-dichloro-β-hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transformations can be used to prepare potentially useful halogenated building blocks. Preliminary mechanistic studies suggest that the reaction involves participation of the acetonitrile solvent in the formation of a 5-halo-1,3-oxazine intermediate.
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spelling pubmed-42716742014-12-22 Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions** D’Oyley, Jarryl M Aliev, Abil E Sheppard, Tom D Angew Chem Int Ed Engl Communications The regioselective conversion of propargylic alcohols into previously unreported α,α-diiodo-β-hydroxyketones was achieved by treatment with N-iodosuccinimide in the presence of a gold catalyst. The corresponding α,α-dichloro-β-hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transformations can be used to prepare potentially useful halogenated building blocks. Preliminary mechanistic studies suggest that the reaction involves participation of the acetonitrile solvent in the formation of a 5-halo-1,3-oxazine intermediate. WILEY-VCH Verlag 2014-09-26 2014-08-21 /pmc/articles/PMC4271674/ /pubmed/25147077 http://dx.doi.org/10.1002/anie.201405348 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by-nc-nd/3.0/ This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
D’Oyley, Jarryl M
Aliev, Abil E
Sheppard, Tom D
Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title_full Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title_fullStr Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title_full_unstemmed Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title_short Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions**
title_sort regioselective dihalohydration reactions of propargylic alcohols: gold-catalyzed and noncatalyzed reactions**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4271674/
https://www.ncbi.nlm.nih.gov/pubmed/25147077
http://dx.doi.org/10.1002/anie.201405348
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