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Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthes...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4734388/ https://www.ncbi.nlm.nih.gov/pubmed/26877817 http://dx.doi.org/10.3762/bjoc.12.16 |
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author | Sterckx, Hans De Houwer, Johan Mensch, Carl Herrebout, Wouter Tehrani, Kourosch Abbaspour Maes, Bert U W |
author_facet | Sterckx, Hans De Houwer, Johan Mensch, Carl Herrebout, Wouter Tehrani, Kourosch Abbaspour Maes, Bert U W |
author_sort | Sterckx, Hans |
collection | PubMed |
description | The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit. |
format | Online Article Text |
id | pubmed-4734388 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-47343882016-02-12 Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen Sterckx, Hans De Houwer, Johan Mensch, Carl Herrebout, Wouter Tehrani, Kourosch Abbaspour Maes, Bert U W Beilstein J Org Chem Full Research Paper The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit. Beilstein-Institut 2016-01-27 /pmc/articles/PMC4734388/ /pubmed/26877817 http://dx.doi.org/10.3762/bjoc.12.16 Text en Copyright © 2016, Sterckx et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Sterckx, Hans De Houwer, Johan Mensch, Carl Herrebout, Wouter Tehrani, Kourosch Abbaspour Maes, Bert U W Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title | Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title_full | Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title_fullStr | Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title_full_unstemmed | Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title_short | Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
title_sort | base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4734388/ https://www.ncbi.nlm.nih.gov/pubmed/26877817 http://dx.doi.org/10.3762/bjoc.12.16 |
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