Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: Reaction scope and limitations

Aleksandra A. Zagulyaeva; Christopher T Banek; Mekhman S. Yusubov; Viktor Zhdankin

doi:10.1021/ol101993q

Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: Reaction scope and limitations

Aleksandra A. Zagulyaeva, Christopher T Banek, Mekhman S. Yusubov, Viktor Zhdankin

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80 Scopus citations

Abstract

Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in aqueous acetonitrile. On the basis of this reaction, a convenient experimental procedure for the preparation of alkylcarbamates using Oxone as the oxidant in the presence of iodobenzene in methanol has been developed. An efficient method for direct conversion of substituted benzamides to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile has also been found.

Original language	English (US)
Pages (from-to)	4644-4647
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	20
DOIs	https://doi.org/10.1021/ol101993q
State	Published - Oct 15 2010

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title = "Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: Reaction scope and limitations",

abstract = "Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in aqueous acetonitrile. On the basis of this reaction, a convenient experimental procedure for the preparation of alkylcarbamates using Oxone as the oxidant in the presence of iodobenzene in methanol has been developed. An efficient method for direct conversion of substituted benzamides to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile has also been found.",

author = "Zagulyaeva, {Aleksandra A.} and Banek, {Christopher T} and Yusubov, {Mekhman S.} and Viktor Zhdankin",

year = "2010",

month = oct,

day = "15",

doi = "10.1021/ol101993q",

language = "English (US)",

volume = "12",

pages = "4644--4647",

journal = "Organic Letters",

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T1 - Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone

T2 - Reaction scope and limitations

AU - Zagulyaeva, Aleksandra A.

AU - Banek, Christopher T

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor

PY - 2010/10/15

Y1 - 2010/10/15

N2 - Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in aqueous acetonitrile. On the basis of this reaction, a convenient experimental procedure for the preparation of alkylcarbamates using Oxone as the oxidant in the presence of iodobenzene in methanol has been developed. An efficient method for direct conversion of substituted benzamides to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile has also been found.

AB - Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from PhI and Oxone in aqueous acetonitrile. On the basis of this reaction, a convenient experimental procedure for the preparation of alkylcarbamates using Oxone as the oxidant in the presence of iodobenzene in methanol has been developed. An efficient method for direct conversion of substituted benzamides to the respective quinone derivatives by treatment with Oxone and iodobenzene in aqueous acetonitrile has also been found.

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DO - 10.1021/ol101993q

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Hofmann rearrangement of carboxamides mediated by hypervalent iodine species generated in situ from iodobenzene and oxone: Reaction scope and limitations

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