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Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions

Tri- or tetrasubstituted furans have been prepared from terminal activated olefins and acyl chlorides or anhydrides by a multicomponental convergent synthesis mode. Instead of stoichiometric nBu(3)P, only catalytic nBu(3)P or nBu(3)P=O is needed to furnish the furans in modest to excellent yields wi...

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Detalles Bibliográficos
Autores principales: Fan, Xia, Chen, Rongshun, Han, Jie, He, Zhengjie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943692/
https://www.ncbi.nlm.nih.gov/pubmed/31888142
http://dx.doi.org/10.3390/molecules24244595
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author Fan, Xia
Chen, Rongshun
Han, Jie
He, Zhengjie
author_facet Fan, Xia
Chen, Rongshun
Han, Jie
He, Zhengjie
author_sort Fan, Xia
collection PubMed
description Tri- or tetrasubstituted furans have been prepared from terminal activated olefins and acyl chlorides or anhydrides by a multicomponental convergent synthesis mode. Instead of stoichiometric nBu(3)P, only catalytic nBu(3)P or nBu(3)P=O is needed to furnish the furans in modest to excellent yields with a good functional group tolerance under the aid of reducing agent silane. This synthetic method features a silane-driven catalytic intramolecular Wittig reaction as a key annulation step and represents the first successful application of catalytic Wittig reaction in multicomponent cascade reaction.
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spelling pubmed-69436922020-01-10 Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions Fan, Xia Chen, Rongshun Han, Jie He, Zhengjie Molecules Article Tri- or tetrasubstituted furans have been prepared from terminal activated olefins and acyl chlorides or anhydrides by a multicomponental convergent synthesis mode. Instead of stoichiometric nBu(3)P, only catalytic nBu(3)P or nBu(3)P=O is needed to furnish the furans in modest to excellent yields with a good functional group tolerance under the aid of reducing agent silane. This synthetic method features a silane-driven catalytic intramolecular Wittig reaction as a key annulation step and represents the first successful application of catalytic Wittig reaction in multicomponent cascade reaction. MDPI 2019-12-16 /pmc/articles/PMC6943692/ /pubmed/31888142 http://dx.doi.org/10.3390/molecules24244595 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Fan, Xia
Chen, Rongshun
Han, Jie
He, Zhengjie
Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title_full Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title_fullStr Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title_full_unstemmed Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title_short Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions
title_sort convergent synthesis of polysubstituted furans via catalytic phosphine mediated multicomponent reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943692/
https://www.ncbi.nlm.nih.gov/pubmed/31888142
http://dx.doi.org/10.3390/molecules24244595
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