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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2012-12, Vol.77 (24), p.11399-11404
Hauptverfasser: Yoshimura, Akira, Middleton, Kyle R, Luedtke, Matthew W, Zhu, Chenjie, Zhdankin, Viktor V
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302375m