Categories: C=O Bond Formation > Synthesis of Ketones
Synthesis of 1,2-diketones
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Recent Literature
A highly efficient and mild procedure for the oxidation of different types of
alcohols uses TEMPO as catalyst, iodobenzene dichloride as stoichiometric
oxidant, and pyridine as base. Oxidation of 1,2-diols gives α-hydroxy ketones or
α-diketones depending on the amount of oxidant used. High yielding procedures
for the preparation of iodoarene dichlorides have been developed.
X.-F. Zhao, C. Zhang, Synthesis, 2007,
551-557.
A Wacker-type oxidation of alkynes catalyzed by PdBr2 and CuBr2
allows an efficient access to 1,2-diketones using molecular oxygen. Under
optimized conditions, various alkynes give 1,2-diketones in good yield. The
mechanism of this reaction was preliminarily investigated by control experiments.
W. Ren, Y. Xia, S.-J. Ji, Y. Zhang, X. Wan, J. Zhao, Org. Lett., 2009,
11, 1841-1844.
Oxidation of alkynes to α-dicarbonyl derivatives through a convenient
one-pot procedure via a Brønsted acid-promoted "hydration" and a DMSO-based
oxidation sequence has been achieved in high yields.
Z. Wan, C. D. Jones, D. Mitchell, J. Y. Pu, T. Y. Zhang, J. Org. Chem.,
2006, 71, 826-828.
The reaction of alkynes with N-iodosuccinimides and water at 70˚C allows
a convenient and practical approach to α-diketones.
M. Niu, H. Fu, Y. Jiang, Y. Zhao, Synthesis, 2008,
2879-2882.
1,3-Diols undergo smooth oxidative cleavage of the C-C bond in the presence of
2-iodoxybenzoic acid (IBX) affording 1,2-diketones in excellent yields under
mild conditions.
J. S. Yadav, S. K. Biswas, R. Srinivas,
Synthesis, 2006, 4237-4241.
