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...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.12.16 |
| _version_ | 1818654866594070528 |
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| author | Hans Sterckx Johan De Houwer Carl Mensch Wouter Herrebout Kourosch Abbaspour Tehrani Bert U. W. Maes |
| author_facet | Hans Sterckx Johan De Houwer Carl Mensch Wouter Herrebout Kourosch Abbaspour Tehrani Bert U. W. Maes |
| author_sort | Hans Sterckx |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-17T03:00:36Z |
| format | Article |
| id | doaj.art-a1dfceda8c8441fead53e26414eca04e |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T03:00:36Z |
| publishDate | 2016-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a1dfceda8c8441fead53e26414eca04e2022-12-21T22:06:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-01-0112114415310.3762/bjoc.12.161860-5397-12-16Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygenHans Sterckx0Johan De Houwer1Carl Mensch2Wouter Herrebout3Kourosch Abbaspour Tehrani4Bert U. W. Maes5Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumDepartment of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumDepartment of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumDepartment of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumDepartment of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumDepartment of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, BelgiumThe 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.https://doi.org/10.3762/bjoc.12.16base metalbenzyliccatalyzedmolecular oxygenoxygenation |
| spellingShingle | Hans Sterckx Johan De Houwer Carl Mensch Wouter Herrebout Kourosch Abbaspour Tehrani Bert U. W. Maes Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen Beilstein Journal of Organic Chemistry base metal benzylic catalyzed molecular oxygen oxygenation |
| 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 | base metal benzylic catalyzed molecular oxygen oxygenation |
| url | https://doi.org/10.3762/bjoc.12.16 |
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