TY - JOUR
T1 - Readily accessible oxazolidine nitroxyl radicals: bifunctional cocatalysts for simplified copper based aerobic oxidation
AU - Gartshore, Christopher
AU - Lupton, David
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
UR - http://onlinelibrary.wiley.com/doi/10.1002/adsc.201000627/pdf
U2 - 10.1002/adsc.201000627
DO - 10.1002/adsc.201000627
M3 - Article
VL - 352
SP - 3321
EP - 3328
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 18
ER -