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

Research output: Contribution to journalArticle

28 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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Carbamates
Oxidants
Iodine
Methanol
potassium peroxymonosulfuric acid
hexafluoroisopropanol
iodobenzene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hypervalent iodine catalyzed hofmann rearrangement of carboxamides using oxone as terminal oxidant. / Yoshimura, Akira; Middleton, Kyle R.; Luedtke, Matthew W.; Zhu, Chenjie; Zhdankin, Viktor V.

In: Journal of Organic Chemistry, Vol. 77, No. 24, 21.12.2012, p. 11399-11404.

Research output: Contribution to journalArticle

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