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

L Huang, K Cheng, B Yao, Y Xie…

Index: Huang, Lehao; Cheng, Kai; Yao, Bangben; Xie, Yongju; Zhang, Yuhong Journal of Organic Chemistry, 2011 , vol. 76, # 14 p. 5732 - 5737

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Citation Number: 47

Abstract

A conceptual method for the preparation of 1, 2-diketones is reported. The selective C–C bond cleavage of 1, 3-diketones affords the 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 the useful 1, 2-diketones.

~70%

~67%

~86%

~61%

~69%

~78%

~82%

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