Title
Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
London ,
Subject
Chemistry
Source (journal)
Beilstein journal of organic chemistry. - London
Volume/pages
12(2016) , p. 144-153
ISSN
1860-5397
ISI
000368653500001
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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. ICPMS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.
Full text (open access)
https://repository.uantwerpen.be/docman/irua/97e4f0/130711.pdf
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