Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in Situ from lodobenzene and Oxone: Reaction Scope and Limitations

被引：73
作者：
Zagulyaeva, Aleksandra A. [1 ]
Banek, Christopher T. [1 ]
Yusubov, Mekhman S. [2 ,3 ]
Zhdankin, Viktor V. [1 ]
机构：
[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA
[2] Siberian State Med Univ, Tomsk 634050, Russia
[3] Tomsk Polytech Univ, Tomsk 634050, Russia
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 20期
基金：
美国国家科学基金会;
关键词：
CONVENIENT SYNTHESIS; DIRECT CONVERSION; ALIPHATIC AMIDES; AMINES; OXIDATIONS; <I; I-BIS(TRIFLUOROACETOXY)IODO>BENZENE; TOSYLATES; REAGENTS; BINDING; ACCESS;
D O I：
10.1021/ol101993q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Alkylcarboxamides can be converted to the respective amines by Hofmann rearrangement using hypervalent iodine species generated in situ from Phl 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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收藏
页码：4644 / 4647
页数：4
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