Iron-Promoted C-C Bond Cleavage of 1,3-Diketones: A Route to 1,2-Diketones under Mild Reaction Conditions

Lehao Huang, Kai Cheng, Bangben Yao, Yongju Xie and Yuhong Zhang*

*Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Email: yhzhangzju.edu.cn

L. Huang, K. Cheng, B. Yao, Y. Xie, Y. Zhang, J. Org. Chem., 2011, 76, 5732-5737.

DOI: 10.1021/jo200840y

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Abstract

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.

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proposed mechanism

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Key Words

1,2-Diketones, tert-Butyl nitrite

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ID: J42-Y2011-2000