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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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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. |
format | Online Article Text |
id | pubmed-6099344 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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