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A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst
Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273256/ https://www.ncbi.nlm.nih.gov/pubmed/27854340 http://dx.doi.org/10.3390/molecules21111539 |
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author | de Souza, Viviane P. Oliveira, Cristiane K. de Souza, Thiago M. Menezes, Paulo H. Alves, Severino Longo, Ricardo L. Malvestiti, Ivani |
author_facet | de Souza, Viviane P. Oliveira, Cristiane K. de Souza, Thiago M. Menezes, Paulo H. Alves, Severino Longo, Ricardo L. Malvestiti, Ivani |
author_sort | de Souza, Viviane P. |
collection | PubMed |
description | Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles. |
format | Online Article Text |
id | pubmed-6273256 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62732562018-12-28 A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst de Souza, Viviane P. Oliveira, Cristiane K. de Souza, Thiago M. Menezes, Paulo H. Alves, Severino Longo, Ricardo L. Malvestiti, Ivani Molecules Article Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles. MDPI 2016-11-16 /pmc/articles/PMC6273256/ /pubmed/27854340 http://dx.doi.org/10.3390/molecules21111539 Text en © 2016 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 de Souza, Viviane P. Oliveira, Cristiane K. de Souza, Thiago M. Menezes, Paulo H. Alves, Severino Longo, Ricardo L. Malvestiti, Ivani A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title | A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title_full | A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title_fullStr | A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title_full_unstemmed | A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title_short | A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst |
title_sort | green approach for allylations of aldehydes and ketones: combining allylborate, mechanochemistry and lanthanide catalyst |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273256/ https://www.ncbi.nlm.nih.gov/pubmed/27854340 http://dx.doi.org/10.3390/molecules21111539 |
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