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Nickel-Catalyzed Formal Aminocarbonylation of Unactivated Alkyl Iodides with Isocyanides

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

*East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China, Email: qujpdlut.edu.cn, yifengchenecust.edu.cn

W. Huang, Y. Wang, Y. Wang, M. Shrestha, J. Qu, Y. Chen, Org. Lett., 2020, 22, 3245-3250.

DOI: 10.1021/acs.orglett.0c01022


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Abstract

A Ni-catalyzed formal aminocarbonylation of primary and secondary unactivated aliphatic iodides with isocyanides provides alkyl amides via a selective monomigratory insertion of isocyanides with alkyl iodides, subsequent β-hydride elimination, and hydrolysis. The reaction features wide functional group tolerance under mild conditions.

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proposed mechanism



Key Words

carboxylation


ID: J54-Y2020