Oxidative Rearrangement of Primary Amines Using PhI(OAc) and CsCO.

Org Lett

Graduate School of Pharmaceutical Sciences , Osaka University, 1-6 Yamada-oka , Suita , Osaka 565-0871 , Japan.

Published: May 2019

An oxidative rearrangement of primary amines mediated by a hypervalent iodine(III) reagent is herein reported. The combination of PhI(OAc) and CsCO proves highly efficient at inducing the direct 1,2-C to N migration of primary amines, which 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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http://dx.doi.org/10.1021/acs.orglett.9b00559DOI Listing

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