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: ayoshimu
d.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
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.
see article for more examples
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
