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Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature

Kengo Hyodo* , Kosuke Togashi, Naoki Oishi, Genna Hasegawa and 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, K. Togashi, N. Oishi, G. Hasegawa, K. Uchida, Org. Lett., 2017, 19, 3005-3008.

DOI: 10.1021/acs.orglett.7b01263 (free Supporting Information)


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Abstract

The use of an O-protected oxime rather than an explosive O-protected hydroxylamine enables a safe, Brønsted acid-catalyzed synthesis of nitriles via O-protected aldoximes through transoximation. The reaction could be performed on a 1 g scale.

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proposed mechanism



Key Words

nitriles


ID: J54-Y2017