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Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)

Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH(3)NH(3), with bio-ba...

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Detalles Bibliográficos
Autores principales: Faverio, Chiara, Boselli, Monica Fiorenza, Camarero Gonzalez, Patricia, Puglisi, Alessandra, Benaglia, Maurizio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8111428/
https://www.ncbi.nlm.nih.gov/pubmed/34025809
http://dx.doi.org/10.3762/bjoc.17.83
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author Faverio, Chiara
Boselli, Monica Fiorenza
Camarero Gonzalez, Patricia
Puglisi, Alessandra
Benaglia, Maurizio
author_facet Faverio, Chiara
Boselli, Monica Fiorenza
Camarero Gonzalez, Patricia
Puglisi, Alessandra
Benaglia, Maurizio
author_sort Faverio, Chiara
collection PubMed
description Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH(3)NH(3), with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.
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spelling pubmed-81114282021-05-21 Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3) Faverio, Chiara Boselli, Monica Fiorenza Camarero Gonzalez, Patricia Puglisi, Alessandra Benaglia, Maurizio Beilstein J Org Chem Letter Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH(3)NH(3), with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated. Beilstein-Institut 2021-05-06 /pmc/articles/PMC8111428/ /pubmed/34025809 http://dx.doi.org/10.3762/bjoc.17.83 Text en Copyright © 2021, Faverio et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Faverio, Chiara
Boselli, Monica Fiorenza
Camarero Gonzalez, Patricia
Puglisi, Alessandra
Benaglia, Maurizio
Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title_full Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title_fullStr Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title_full_unstemmed Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title_short Nitroalkene reduction in deep eutectic solvents promoted by BH(3)NH(3)
title_sort nitroalkene reduction in deep eutectic solvents promoted by bh(3)nh(3)
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8111428/
https://www.ncbi.nlm.nih.gov/pubmed/34025809
http://dx.doi.org/10.3762/bjoc.17.83
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