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

Aleksandra A. Zagulyaeva, Christopher T. Banek, Mekhman S. Yusubov and Viktor V. Zhdankin*

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

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

DOI: 10.1021/ol101993q

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Abstract

Alkylcarboxamides can be converted to the respective alkylcarbamates by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in methanol. In addition, substituted benzamides can be converted to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile.

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

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

(Tosylimino)phenyl-λ³-iodane as a Reagent for the Synthesis of Methyl Carbamates via Hofmann Rearrangement of Aromatic and Aliphatic Carboxamides

A. Yoshimura, M. W. Luedtke, V. V. Zhdankin, J. Org. Chem., 2012, 77, 2087-2091.

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Key Words

Hofmann Rearrangement, Carbamates, Hypervalent Iodine Compounds, Oxone

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ID: J54-Y2010-2920