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Wacker-Type Oxidation of Alkynes into 1,2-Diketones Using Molecular Oxygen

Wei Ren, Yuanzhi Xia, Shun-Jun Ji, Yong Zhang, Xiaobing Wan* and Jing Zhao

*Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China, Email: wanxbsuda.edu.cn

W. Ren, Y. Xia, S.-J. Ji, Y. Zhang, X. Wan, J. Zhao, Org. Lett., 2009, 11, 1841-1844.

DOI: 10.1021/ol900344g (free Supporting Information)


Abstract

A Wacker-type oxidation of alkynes catalyzed by PdBr2 and CuBr2 allows an efficient access to 1,2-diketones using molecular oxygen. Under optimized conditions, various alkynes give 1,2-diketones in good yield. The mechanism of this reaction was preliminarily investigated by control experiments.

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Key Words

Wacker-Tsuji Oxidation, 1,2-Diketones, Oxygen


ID: J54-Y2009-1350