Synthesis of 1,2-diketones
A versatile and highly efficient method for the direct synthesis of α-keto esters and 1,2-diketones utilizes an oxidative cleavage of various β-keto esters and 1,3-diketones by an Oxone/aluminum trichloride system. The simple, environmentally benign one-step oxidation reaction proceeded selectively in aqueous media to afford products in high yields and short reaction times.
A. Stergiou, A. Bariotaki, D. Kalaitzakis, I. Smonou, J. Org. Chem., 2013, 78, 7268-7273.
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.