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A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors
In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7249194/ https://www.ncbi.nlm.nih.gov/pubmed/32357472 http://dx.doi.org/10.3390/molecules25092018 |
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author | Nacca, Francesca Giulia Monti, Bonifacio Lenardão, Eder João Evans, Paul Santi, Claudio |
author_facet | Nacca, Francesca Giulia Monti, Bonifacio Lenardão, Eder João Evans, Paul Santi, Claudio |
author_sort | Nacca, Francesca Giulia |
collection | PubMed |
description | In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic α,β-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive β-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, α,β-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7° recycling rounds). |
format | Online Article Text |
id | pubmed-7249194 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72491942020-06-10 A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors Nacca, Francesca Giulia Monti, Bonifacio Lenardão, Eder João Evans, Paul Santi, Claudio Molecules Article In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic α,β-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive β-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, α,β-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7° recycling rounds). MDPI 2020-04-26 /pmc/articles/PMC7249194/ /pubmed/32357472 http://dx.doi.org/10.3390/molecules25092018 Text en © 2020 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 Nacca, Francesca Giulia Monti, Bonifacio Lenardão, Eder João Evans, Paul Santi, Claudio A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title | A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title_full | A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title_fullStr | A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title_full_unstemmed | A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title_short | A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors |
title_sort | simple zinc-mediated method for selenium addition to michael acceptors |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7249194/ https://www.ncbi.nlm.nih.gov/pubmed/32357472 http://dx.doi.org/10.3390/molecules25092018 |
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