Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction

Cyclic β‐oxo esters are converted with enol acetates in a cerium‐catalyzed, oxidative Umpolung reaction to furnish 1,4‐diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of...

Descripción completa

Detalles Bibliográficos
Autores principales: Geibel, Irina, Christoffers, Jens
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY‐VCH Verlag 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4762319/
http://dx.doi.org/10.1002/ejoc.201600057
_version_ 1782417094261866496
author Geibel, Irina
Christoffers, Jens
author_facet Geibel, Irina
Christoffers, Jens
author_sort Geibel, Irina
collection PubMed
description Cyclic β‐oxo esters are converted with enol acetates in a cerium‐catalyzed, oxidative Umpolung reaction to furnish 1,4‐diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C–C coupling reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl(3) ·7H(2)O as precatalyst.
format Online
Article
Text
id pubmed-4762319
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher WILEY‐VCH Verlag
record_format MEDLINE/PubMed
spelling pubmed-47623192016-05-25 Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction Geibel, Irina Christoffers, Jens European J Org Chem Communications Cyclic β‐oxo esters are converted with enol acetates in a cerium‐catalyzed, oxidative Umpolung reaction to furnish 1,4‐diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C–C coupling reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl(3) ·7H(2)O as precatalyst. WILEY‐VCH Verlag 2016-01-29 2016-02 /pmc/articles/PMC4762319/ http://dx.doi.org/10.1002/ejoc.201600057 Text en © 2016 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non‐Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. Open access.
spellingShingle Communications
Geibel, Irina
Christoffers, Jens
Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title_full Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title_fullStr Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title_full_unstemmed Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title_short Synthesis of 1,4‐Diketones from β‐Oxo Esters and Enol Acetates by ­Cerium‐Catalyzed Oxidative Umpo­lung Reaction
title_sort synthesis of 1,4‐diketones from β‐oxo esters and enol acetates by ­cerium‐catalyzed oxidative umpo­lung reaction
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4762319/
http://dx.doi.org/10.1002/ejoc.201600057
work_keys_str_mv AT geibelirina synthesisof14diketonesfromboxoestersandenolacetatesbyceriumcatalyzedoxidativeumpolungreaction
AT christoffersjens synthesisof14diketonesfromboxoestersandenolacetatesbyceriumcatalyzedoxidativeumpolungreaction

Ejemplares similares