A Mild and Efficient Direct α-Amination of β-Dicarbonyl Compounds Using Iodosobenzene and p-Toluenesulfonamide Catalyzed by Perchlorate Zinc Hexahydrate

Jun Yu, Shan-Shan Liu, Jian Cui, Xue-Sen Hou and Chi Zhang*

*State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, Email: zhangchinankai.edu.cn

J. Yu, S.-S. Liu, J. Cui, X.-S. Hou, C. Zhang, Org. Lett., 2012, 14, 832-835.

DOI: 10.1021/ol203358f

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Abstract

The use of iodosobenzene (PhIO) as oxidant and p-toluenesulfonamide (TsNH₂) as aminating reagent in the presence of a catalytic amount of perchlorate zinc hexahydrate enables a direct α-amination of β-dicarbonyl compounds. The reaction proceeds quickly at rt to provide the corresponding α-N-tosylamido β-dicarbonyl compounds very good yields.

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Key Words

α-amination, sulfonamides, iodosobenzene

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ID: J54-Y2012-0320