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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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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. |
format | Online Article Text |
id | pubmed-9017099 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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