Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
Kengo Hyodo*, Genna Hasegawa, Hiroya Maki, Kingo Uchida
*Department of Material Chemistry, Faculty of Science and Technology, Ryukoku University, Seta, Otsu, Shiga 520-2194, Japan,
Email: hyodo
rins.ryukoku.ac.jp
K. Hyodo, G. Hasegawa, H. Maki, K. Uchida, Org. Lett., 2019, 21, 2818-2822.
DOI: 10.1021/acs.orglett.9b00807
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Abstract
An oxime reagent as an amino group source achieves a direct conversion from acetyl arenes and alkanes to primary amines with C-C bond cleavage via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as rolipram and baclophen.
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proposed mechanism
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K. Hyodo, G. Hasegawa, N. Oishi, K. Kuroda, K. Uchida, J. Org. Chem., 2018, 83, 13080-13087.
Key Words
anilines, primary amines, Beckmann rearrangement, Pinner reaction
ID: J54-Y2019
