Oxidative Rearrangement of Primary Amines Using PhI(OAc)₂ and Cs₂CO₃

Wataru Yamakoshi, Mitsuhiro Arisawa, Kenichi Murai*

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan, Email: muraiphs.osaka-u.ac.jp

W. Yamakoshi, M. Arisawa, K. Murai, Org. Lett., 2019, 21, 3023-3027.

DOI: 10.1021/acs.orglett.9b00559

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Abstract

The combination of PhI(OAc)₂ and Cs₂CO₃ mediates an efficient oxidative 1,2-C to N migration of primary amines. The reaction can be applied to the preparation of both acyclic and cyclic amines. A mechanistic study shows that the rearrangement proceeds via a concerted mechanism.

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Key Words

aryl amines, PIDA, sodium borohydride

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ID: J54-Y2019