Readily accessible oxazolidine nitroxyl radicals: bifunctional cocatalysts for simplified copper based aerobic oxidation

Christopher Gartshore, David Lupton

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

Using a two-step procedure a range of bifunctional oxazolidine nitroxyl radicals have been prepared. The application of these co-catalysts to the copper-based aerobic oxidation of alcohols was then investigated. From these studies it was found that the parent tetramethyloxazolidine nitroxyl radical L1 was competent for oxidation in the presence of 2,2 -bipyridine, and the bifunctional pyridyl-containing nitroxyl radicals L2 and L3 could be used in the absence of additional coordinating ligands. Following optimization, the scope of this simplified transformation was explored, demonstrating that a range of primary and secondary benzylic alcohols are readily oxidized. In addition, the oxidation of allylic alcohols and hydroquinone can be achieved.
Original languageEnglish
Pages (from-to)3321 - 3328
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume352
Issue number18
DOIs
Publication statusPublished - 2010

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