20121-93-1Relevant academic research and scientific papers
Preparation of acyloins by cerium-catalyzed, direct hydroxylation of β-dicarbonyl compounds with molecular oxygen
Christoffers, Jens,Werner, Thomas,Unger, Sven,Frey, Wolfgang
, p. 425 - 431 (2003)
We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a-4i give high yields of analytically pure products 5a-5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j-4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j-5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Cerium-catalyzed α-oxidation of β-dicarbonyl compounds with molecular oxygen
Christoffers,Werner
, p. 119 - 121 (2007/10/03)
β-Ketoesters and β-diketones are α-hydroxylated by molecular oxygen in the presence of 5 mol% CECl3-7 H2O in i-PrOH as solvent. The method is limited to substrates with an α-alkyl substituent. Optimal yields are achieved with cyclic
