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Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen (2016)

Hans Sterckx, Johan De Houwer, Carl Mensch, Wouter Herrebout, Kourosch Abbaspour Tehrani and Bert U. W. Maes

Beilstein-Institut

In: Beilstein Journal of Organic Chemistry

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Publication Date: 2016-01-28

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. Beilstein J. Org. Chem. 2016, 12, 144–153. doi:10.3762/bjoc.12.16

Keywords: base metalbenzyliccatalyzedmolecular oxygenoxygenation

Electronic ISSN: 1860-5397

Topics: Chemistry and Pharmacology