Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids

[Image: see text] An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the pre...

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Autores principales: Raji Reddy, Chada, Subbarao, Muppidi, Kolgave, Dattahari H., Ajaykumar, Uprety, Vinaya, Puthiya Purayil
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9608386/
https://www.ncbi.nlm.nih.gov/pubmed/36312410
http://dx.doi.org/10.1021/acsomega.2c05394
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author Raji Reddy, Chada
Subbarao, Muppidi
Kolgave, Dattahari H.
Ajaykumar, Uprety
Vinaya, Puthiya Purayil
author_facet Raji Reddy, Chada
Subbarao, Muppidi
Kolgave, Dattahari H.
Ajaykumar, Uprety
Vinaya, Puthiya Purayil
author_sort Raji Reddy, Chada
collection PubMed
description [Image: see text] An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the presence of potassium persulfate (K(2)S(2)O(8)) as the oxidant. Further, this approach was extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively. The present three-component method offers the diverse substitutions on selenium involving two C–Se and one C–C bond formations.
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spelling pubmed-96083862022-10-28 Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids Raji Reddy, Chada Subbarao, Muppidi Kolgave, Dattahari H. Ajaykumar, Uprety Vinaya, Puthiya Purayil ACS Omega [Image: see text] An efficient and straightforward synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. The reaction proceeds through silver-catalyzed oxidative dearomatization in the presence of potassium persulfate (K(2)S(2)O(8)) as the oxidant. Further, this approach was extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively. The present three-component method offers the diverse substitutions on selenium involving two C–Se and one C–C bond formations. American Chemical Society 2022-10-10 /pmc/articles/PMC9608386/ /pubmed/36312410 http://dx.doi.org/10.1021/acsomega.2c05394 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Raji Reddy, Chada
Subbarao, Muppidi
Kolgave, Dattahari H.
Ajaykumar, Uprety
Vinaya, Puthiya Purayil
Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title_full Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title_fullStr Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title_full_unstemmed Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title_short Access to Diverse Seleno-spirocyclohexadienones via Ag(II)-Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
title_sort access to diverse seleno-spirocyclohexadienones via ag(ii)-catalyzed selenylative ipso-annulation with se and boronic acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9608386/
https://www.ncbi.nlm.nih.gov/pubmed/36312410
http://dx.doi.org/10.1021/acsomega.2c05394
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