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Hypervalent Iodine-Mediated Beckmann Rearrangement of Ketoximes

Ryohei Oishi, Kazutoshi Segi, Hiromi Hamamoto, Akira Nakamura, Tomohiro Maegawa *, Yasuyoshi Miki*

*School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan, Email: maegawaphar.kindai.ac.jp, y_mikiphar.kindai.ac.jp

R. Oishi, K. Segi, H. Hamamoto, A. Nakamura, T. Maegawa, Y. Miki, Synlett, 2018, 29, 1465-1468.

DOI: 10.1055/s-0037-1609686 (free Supporting Information)


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Abstract

Whereas the reaction of ketoximes with hypervalent iodine afforded the corresponding ketone, premixing of hypervalent iodine and a Lewis acid was effective for promoting the Beckmann rearrangement of aromatic and aliphatic ketoximes into their corresponding amides in very good yields.

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Key Words

PIDA, Beckmann rearrangement, oxime, amide, Lewis acid


ID: J60-Y2018