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Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant

Akira Yoshimura*, Kyle R. Middleton, Matthew W. Luedtke, Chenjie Zhu and Viktor V. Zhdankin*

*Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota, 55812, United States, Email: ayoshimud.umn.edu, vzhdankid.umn.edu

A. Yoshimura, K. R. Middleton, M. W. Luedtke, C. Zhu, V. V. Zhdankin, J. Org. Chem., 2012, 77, 11399-11404.

DOI: 10.1021/jo302375m (free Supporting Information)


Abstract

Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene via hypervalent iodine species generated in situ in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) in aqueous methanol solutions. Under these conditions, Hofmann rearrangement of various carboxamides affords corresponding carbamates in high yields.


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Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in Situ from Iodobenzene and Oxone: Reaction Scope and Limitations

A. A. Zagulyaeva, C. T. Banek, M. S. Yusubov, V. V. Zhdankin, Org. Lett., 2010, 12, 4644-4647.


Key Words

Hofmann Rearrangement, Carbamates, Hypervalent Iodine Compounds, Oxone


ID: J42-Y2012-3950