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镍催化未活化碘代烷烃与异腈的形式氨基羰基化反应。

Nickel-Catalyzed Formal Aminocarbonylation of Unactivated Alkyl Iodides with Isocyanides.

作者信息

Huang Wenyi, Wang Yun, Weng Yangyang, Shrestha Mohini, Qu Jingping, Chen Yifeng

机构信息

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.

出版信息

Org Lett. 2020 Apr 17;22(8):3245-3250. doi: 10.1021/acs.orglett.0c01022. Epub 2020 Apr 3.

Abstract

Herein, we disclose a Ni-catalyzed formal aminocarbonylation of primary and secondary unactivated aliphatic iodides with isocyanides to afford alkyl amide, which proceeds via the selective monomigratory insertion of isocyanides with alkyl iodides, subsequent β-hydride elimination, and hydrolysis process. The reaction features wide functional group tolerance under mild conditions. Additionally, the selective, one-pot hydrolysis of reaction mixture under acid conditions allows for expedient synthesis of the corresponding alkyl carboxylic acid.

摘要

在此,我们报道了一种镍催化的伯、仲未活化脂肪族碘化物与异腈的形式氨基羰基化反应,以生成烷基酰胺,该反应通过异腈与烷基碘化物的选择性单迁移插入、随后的β-氢消除和水解过程进行。该反应在温和条件下具有广泛的官能团耐受性。此外,反应混合物在酸性条件下的选择性一锅水解能够方便地合成相应的烷基羧酸。

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