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Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules

In this paper we outline how dihalohydration reactions of propargylic alcohols can be used to access a wide variety of useful halogenated building blocks. A novel procedure for dibromohydration of alkynes has been developed, and a selection of dichloro and dibromo diols and cyclic ethers were synthe...

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Detalles Bibliográficos
Autores principales: Gibson, Samantha M., D'Oyley, Jarryl M., Higham, Joe I., Sanders, Kate, Laserna, Victor, Aliev, Abil E., Sheppard, Tom D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099344/
https://www.ncbi.nlm.nih.gov/pubmed/30147439
http://dx.doi.org/10.1002/ejoc.201800668
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author Gibson, Samantha M.
D'Oyley, Jarryl M.
Higham, Joe I.
Sanders, Kate
Laserna, Victor
Aliev, Abil E.
Sheppard, Tom D.
author_facet Gibson, Samantha M.
D'Oyley, Jarryl M.
Higham, Joe I.
Sanders, Kate
Laserna, Victor
Aliev, Abil E.
Sheppard, Tom D.
author_sort Gibson, Samantha M.
collection PubMed
description In this paper we outline how dihalohydration reactions of propargylic alcohols can be used to access a wide variety of useful halogenated building blocks. A novel procedure for dibromohydration of alkynes has been developed, and a selection of dichloro and dibromo diols and cyclic ethers were synthesized. The dihalohydration of homo‐propargylic alcohols provides a useful route to 3‐halofurans, which were shown to readily undergo cycloaddition reactions under mild conditions. Finally, a novel ring expansion of propargylic alcohols containing a cyclopropylalkyne provides access to halogenated alkenylcyclobutanes.
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spelling pubmed-60993442018-08-23 Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules Gibson, Samantha M. D'Oyley, Jarryl M. Higham, Joe I. Sanders, Kate Laserna, Victor Aliev, Abil E. Sheppard, Tom D. European J Org Chem Full Papers In this paper we outline how dihalohydration reactions of propargylic alcohols can be used to access a wide variety of useful halogenated building blocks. A novel procedure for dibromohydration of alkynes has been developed, and a selection of dichloro and dibromo diols and cyclic ethers were synthesized. The dihalohydration of homo‐propargylic alcohols provides a useful route to 3‐halofurans, which were shown to readily undergo cycloaddition reactions under mild conditions. Finally, a novel ring expansion of propargylic alcohols containing a cyclopropylalkyne provides access to halogenated alkenylcyclobutanes. John Wiley and Sons Inc. 2018-07-18 2018-08-07 /pmc/articles/PMC6099344/ /pubmed/30147439 http://dx.doi.org/10.1002/ejoc.201800668 Text en © 2018 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Gibson, Samantha M.
D'Oyley, Jarryl M.
Higham, Joe I.
Sanders, Kate
Laserna, Victor
Aliev, Abil E.
Sheppard, Tom D.
Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title_full Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title_fullStr Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title_full_unstemmed Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title_short Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules
title_sort dihalohydration of alkynols: a versatile approach to diverse halogenated molecules
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099344/
https://www.ncbi.nlm.nih.gov/pubmed/30147439
http://dx.doi.org/10.1002/ejoc.201800668
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