Oxidative Rearrangement of Secondary Amines Using Hypervalent Iodine(III) Reagent
Kenichi Murai1, Tetsuya Kobayashi1, Makoto Miyoshi1
1Graduate School of Pharmaceutical Sciences , Osaka University , 1-6 Yamada-oka , Suita , Osaka 565-0871 , Japan.
Abstract:
A hypervalent iodine(III) reagent mediated oxidative skeletal rearrangement reaction of secondary amines is reported. The transformation, which uses PhI(OAc)2 in CF3CH2OH, was found to be highly efficient at inducing the direct 1,2-C-to-N migration of secondary amines. This method offers facile and divergent access to polycyclic and macrocyclic indole-fused compounds. The synthetic potential of the method is also demonstrated through its application to several substrates, including secondary as well as primary amines.
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