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

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

doi:10.1021/jo302375m

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

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

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53 Scopus citations

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 language	English (US)
Pages (from-to)	11399-11404
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	77
Issue number	24
DOIs	https://doi.org/10.1021/jo302375m
State	Published - Dec 21 2012

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title = "Hypervalent iodine catalyzed hofmann rearrangement of carboxamides using oxone as terminal oxidant",

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.",

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year = "2012",

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language = "English (US)",

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journal = "Journal of Organic Chemistry",

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AU - Yoshimura, Akira

AU - Middleton, Kyle R.

AU - Luedtke, Matthew W.

AU - Zhu, Chenjie

AU - Zhdankin, Viktor

PY - 2012/12/21

Y1 - 2012/12/21

N2 - 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.

AB - 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.

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

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