Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

The reaction of bromopropargylic alcohols with phenols in the presence of Cs(2)CO(3)/DMF affords α-phenoxy-α’-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxol...

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Autores principales: Volostnykh, Ol'ga G, Shemyakina, Olesya A, Stepanov, Anton V, Ushakov, Igor' A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9039521/
https://www.ncbi.nlm.nih.gov/pubmed/35529892
http://dx.doi.org/10.3762/bjoc.18.44
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author Volostnykh, Ol'ga G
Shemyakina, Olesya A
Stepanov, Anton V
Ushakov, Igor' A
author_facet Volostnykh, Ol'ga G
Shemyakina, Olesya A
Stepanov, Anton V
Ushakov, Igor' A
author_sort Volostnykh, Ol'ga G
collection PubMed
description The reaction of bromopropargylic alcohols with phenols in the presence of Cs(2)CO(3)/DMF affords α-phenoxy-α’-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxolan-2-ones, generated in situ from bromopropargylic alcohols and Cs(2)CO(3).
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spelling pubmed-90395212022-05-05 Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones Volostnykh, Ol'ga G Shemyakina, Olesya A Stepanov, Anton V Ushakov, Igor' A Beilstein J Org Chem Full Research Paper The reaction of bromopropargylic alcohols with phenols in the presence of Cs(2)CO(3)/DMF affords α-phenoxy-α’-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxolan-2-ones, generated in situ from bromopropargylic alcohols and Cs(2)CO(3). Beilstein-Institut 2022-04-12 /pmc/articles/PMC9039521/ /pubmed/35529892 http://dx.doi.org/10.3762/bjoc.18.44 Text en Copyright © 2022, Volostnykh et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Volostnykh, Ol'ga G
Shemyakina, Olesya A
Stepanov, Anton V
Ushakov, Igor' A
Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title_full Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title_fullStr Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title_full_unstemmed Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title_short Cs(2)CO(3)-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones
title_sort cs(2)co(3)-promoted reaction of tertiary bromopropargylic alcohols and phenols in dmf: a novel approach to α-phenoxyketones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9039521/
https://www.ncbi.nlm.nih.gov/pubmed/35529892
http://dx.doi.org/10.3762/bjoc.18.44
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