Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of 1,2-diketones
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Name Reactions
Recent Literature
A convenient Pd-catalyzed reaction of aryl halides, tert-butyl isocyanide as the CO
source, and organoaluminum reagents provides 1,2-diketones in very good yields
and with good
functional group tolerance.
B. Chen, X.-F. Wu,
Org. Lett., 2020, 22, 636-641.
A selective C-C bond cleavage of 1,3-diketones affords 1,2-diketones in high
yields under mild reaction conditions in air by the use of FeCl3 as
the catalyst and tert-butyl nitrite (TBN) as the oxidant without the use
of solvent. The possible reaction mechanism is discussed. This protocol provides
an expeditious route to useful 1,2-diketones.
L. Huang, K. Cheng, B. Yao, Y. Xie, Y. Zhang, J. Org. Chem., 2011,
76, 5732-5737.
Iodine/base-catalyzed aerobic photooxidation of 1,3-diketones under
visible-light irradiation of fluorescent lamp enables a catalytic direct
synthesis of 1,2-diketones.
N. Tada, M. Shomura, H. Nakayama, T. Miura, A. Itoh, Synlett, 2010,
1979-1983.
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.
Related
An aerobic decomposition of 1,3-diaryl-2-diazo-1,3-diketones to
1,2-diaryl-1,2-diketones (benzils) can be catalyzed by a few dirhodium
carboxylates (5 mol %) under a balloon pressure of oxygen at ambient
temperatures. An oxygen atom from O2 is shown to be incorporated into
the product accompanied by the extrusion of a carbonyl unit from the starting
materials.
J.-L. Zhu, Y.-T. Tsai, J. Org. Chem., 2021, 86,
813-828.