Hofmann-Type Rearrangement of Imides by in Situ Generation of Imide-Hypervalent Iodines(III) from Iodoarenes

被引：49

作者：

Moriyama, Katsuhiko ^{[1
]}

Ishida, Kazuma ^{[1
]}

Togo, Hideo ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 03期

关键词：

M-CHLOROPERBENZOIC ACID; P-TOLUENESULFONIC ACID; ONE-POT PREPARATION; ALPHA-TOSYLOXYLATION; ORGANOHYPERVALENT IODINE; CATALYTIC VERSION; ANTHRANILIC ACID; FACILE SYNTHESIS; KETONES; CONVERSION;

D O I：

10.1021/ol300028j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from Phl, m-CPBA, and TsOH center dot H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-lambda(3)-iodane intermediate.

引用

页码：946 / 949

页数：4

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