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.
Aerobic oxidation of deoxybenzoins is efficiently catalyzed by
1,4-diazabicyclo[2.2.2]octane (DABCO) with air as the sole oxidant to give the
corresponding benzils in excellent yields. The process has been successfully
extended to a one-pot synthesis of quinoxalines from benzyl ketones and aromatic
1,2-diamines.
C. Qi, H. Jiang, L. Huang, Z. Chen, H. Chen, Synthesis, 2011,
387-396.
Natural sunlight and air are enable an efficient oxidation of α-aryl halogen
derivatives to the corresponding α-aryl carbonyl compounds at room temperature
through the combination of photocatalysis and organocatalysis. A plausible
mechanism was proposed on the basis of the mechanistic studies.
Y. Su, L. Zhang, N. Jiao, Org. Lett., 2011,
13, 2168-2171.
A ruthenium-catalyzed oxidation of alkenes allows an efficient route to
α-diketones using TBHP as an oxidant, is highly functional group tolerant and
practically convenient, requires no additional ligand, and operates under mild
conditions with short reaction times. Based upon experimental observations, a
plausible mechanism is proposed.
S. Chen, Z. Liu, E. Shi, L. Chen, W. Wei, H. Li, Y. Cheng, X. Wan, Org. Lett., 2011,
13, 2274-2277.
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 using ammonium persulfate and diphenyl diselenide as
catalyst in aqueous media leads to 1,2-unprotected dicarbonyl derivatives or to
hemiacetals starting from terminal alkynes.
S. Santoro, B. Battistelli, B. Gjoka, C.-w. S. Si, L. Testaferri, M. Tiecco, C.
Santi, Synlett, 2010,
1402-1406.
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.
