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Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

Jia-Liang Zhu* and Yi-Ting Tsai

*Department of Chemistry, National Dong Hwa University, No. 1, Sec. 2, Da Hsueh Rd., Shoufeng, Hualien 97401, Taiwan, ROC, Email:

J.-L. Zhu, Y.-T. Tsai, J. Org. Chem., 2021, 86, 813-828.

DOI: 10.1021/acs.joc.0c02366

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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.

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proposed mechanisms via a ketene intermediate

Key Words

1,2-diketones, oxidation, oxygen

ID: J42-Y2021