Hypervalent iodine catalyzed hofmann rearrangement of carboxamides using oxone as terminal oxidant

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

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32 Citations (Scopus)

Abstract

Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene. This reaction involves hypervalent iodine species generated in situ from catalytic amount of PhI and Oxone 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.

Original languageEnglish
Pages (from-to)11399-11404
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number24
DOIs
Publication statusPublished - 21 Dec 2012
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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