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...

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Autores principales: Sterckx, Hans, De Houwer, Johan, Mensch, Carl, Herrebout, Wouter, Tehrani, Kourosch Abbaspour, Maes, Bert U W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
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.
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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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