通过碘代芳烃原位生成酰亚胺高价碘(III)实现酰亚胺的霍夫曼型重排。
Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes.
机构信息
Department of Chemistry, Graduate School of Science, Chiba University, Chiba 263-8522, Japan.
出版信息
Org Lett. 2012 Feb 3;14(3):946-9. doi: 10.1021/ol300028j. Epub 2012 Jan 24.
The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H(2)O 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-λ(3)-iodane intermediate.
使用从 PhI、m-CPBA 和 TsOH·H(2)O 原位生成的高价碘(III)试剂进行的芳族和脂肪族酰亚胺的霍夫曼型重排，在醇中存在碱的情况下进行，分别以高产率提供邻氨基苯甲酸衍生物和氨基酸衍生物。该反应通过醇解和随后通过形成酰亚胺-λ(3)-碘烷中间物促进的霍夫曼重排的串联反应进行。
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