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One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow

[Image: see text] The Adler–Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction con...

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Autores principales: Rosatella, Andreia A., Afonso, Carlos A. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9017099/
https://www.ncbi.nlm.nih.gov/pubmed/35449962
http://dx.doi.org/10.1021/acsomega.1c05559
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author Rosatella, Andreia A.
Afonso, Carlos A. M.
author_facet Rosatella, Andreia A.
Afonso, Carlos A. M.
author_sort Rosatella, Andreia A.
collection PubMed
description [Image: see text] The Adler–Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler–Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions.
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spelling pubmed-90170992022-04-20 One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow Rosatella, Andreia A. Afonso, Carlos A. M. ACS Omega [Image: see text] The Adler–Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler–Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions. American Chemical Society 2022-03-31 /pmc/articles/PMC9017099/ /pubmed/35449962 http://dx.doi.org/10.1021/acsomega.1c05559 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 Rosatella, Andreia A.
Afonso, Carlos A. M.
One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title_full One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title_fullStr One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title_full_unstemmed One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title_short One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow
title_sort one-pot transformation of salicylaldehydes to spiroepoxydienones via the adler–becker reaction in a continuous flow
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9017099/
https://www.ncbi.nlm.nih.gov/pubmed/35449962
http://dx.doi.org/10.1021/acsomega.1c05559
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