Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)

A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K(2)S(2)O(8) as oxidant and proceeds in DMSO/H(2)O at en...

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Detalles Bibliográficos
Autores principales: Liu, Qiang, Lu, Weibang, Xie, Guanqun, Wang, Xiaoxia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7431760/
https://www.ncbi.nlm.nih.gov/pubmed/32831954
http://dx.doi.org/10.3762/bjoc.16.164
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author Liu, Qiang
Lu, Weibang
Xie, Guanqun
Wang, Xiaoxia
author_facet Liu, Qiang
Lu, Weibang
Xie, Guanqun
Wang, Xiaoxia
author_sort Liu, Qiang
collection PubMed
description A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K(2)S(2)O(8) as oxidant and proceeds in DMSO/H(2)O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields.
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spelling pubmed-74317602020-08-21 Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8) Liu, Qiang Lu, Weibang Xie, Guanqun Wang, Xiaoxia Beilstein J Org Chem Letter A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K(2)S(2)O(8) as oxidant and proceeds in DMSO/H(2)O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields. Beilstein-Institut 2020-08-12 /pmc/articles/PMC7431760/ /pubmed/32831954 http://dx.doi.org/10.3762/bjoc.16.164 Text en Copyright © 2020, Liu et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Liu, Qiang
Lu, Weibang
Xie, Guanqun
Wang, Xiaoxia
Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title_full Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title_fullStr Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title_full_unstemmed Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title_short Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K(2)S(2)O(8)
title_sort metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by k(2)s(2)o(8)
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7431760/
https://www.ncbi.nlm.nih.gov/pubmed/32831954
http://dx.doi.org/10.3762/bjoc.16.164
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