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Readily Accessible Oxazolidine Nitroxyl Radicals: Bifunctional Cocatalysts for Simplified Copper Based Aerobic Oxidation
Author(s) -
Gartshore Christopher J.,
Lupton David W.
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000627
Subject(s) - chemistry , bifunctional , oxazolidine , nitroxyl , radical , alcohol oxidation , hydroquinone , allylic rearrangement , catalysis , organic chemistry , photochemistry , combinatorial chemistry , polymer chemistry
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.