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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: hyodorins.ryukoku.ac.jp

K. Hyodo, G. Hasegawa, H. Maki, K. Uchida, Org. Lett., 2019, 21, 2818-2822.

DOI: 10.1021/acs.orglett.9b00807 (free Supporting Information)


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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



Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions

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