Sonogashira–Hagihara reactions of halogenated glycals

Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refun...

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Detalles Bibliográficos
Autores principales: Koester, Dennis C, Werz, Daniel B
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/PMC3388853/
https://www.ncbi.nlm.nih.gov/pubmed/23015813
http://dx.doi.org/10.3762/bjoc.8.75
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author Koester, Dennis C
Werz, Daniel B
author_facet Koester, Dennis C
Werz, Daniel B
author_sort Koester, Dennis C
collection PubMed
description Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2.
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spelling pubmed-33888532012-09-26 Sonogashira–Hagihara reactions of halogenated glycals Koester, Dennis C Werz, Daniel B Beilstein J Org Chem Full Research Paper Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2. Beilstein-Institut 2012-05-02 /pmc/articles/PMC3388853/ /pubmed/23015813 http://dx.doi.org/10.3762/bjoc.8.75 Text en Copyright © 2012, Koester and Werz 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
Koester, Dennis C
Werz, Daniel B
Sonogashira–Hagihara reactions of halogenated glycals
title Sonogashira–Hagihara reactions of halogenated glycals
title_full Sonogashira–Hagihara reactions of halogenated glycals
title_fullStr Sonogashira–Hagihara reactions of halogenated glycals
title_full_unstemmed Sonogashira–Hagihara reactions of halogenated glycals
title_short Sonogashira–Hagihara reactions of halogenated glycals
title_sort sonogashira–hagihara reactions of halogenated glycals
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3388853/
https://www.ncbi.nlm.nih.gov/pubmed/23015813
http://dx.doi.org/10.3762/bjoc.8.75
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