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
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Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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container_end_page 11404
container_issue 24
container_start_page 11399
container_title Journal of organic chemistry
container_volume 77
creator Yoshimura, Akira
Middleton, Kyle R
Luedtke, Matthew W
Zhu, Chenjie
Zhdankin, Viktor V
description 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.
doi_str_mv 10.1021/jo302375m
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Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
title Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant
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