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Synthesis 2020; 52(22): 3466-3472
DOI: 10.1055/s-0040-1707229
paper
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Qiao Li
,
Hongwei Jin
,
Yunkui Liu∗
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   eMail: ykuiliu@zjut.edu.cn   eMail: zhoubw@zjut.edu.cn
,
Bingwei Zhou  ∗
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   eMail: ykuiliu@zjut.edu.cn   eMail: zhoubw@zjut.edu.cn
› InstitutsangabenWe are grateful to the Natural Science Foundation of Zhejiang Province (LQ20B020012), the research foundation of Zhejiang University of Technology (2019101000429), and the National Natural Science Foundation of China (No. 21772176 and 21372201) for financial support.
Weitere Informationen

Publikationsverlauf

Received: 23. Juni 2020

Accepted after revision: 03. Juli 2020

Publikationsdatum:
05. August 2020 (online)

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Abstract

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

Key words

nickel catalysis - isocyanide - alkyl halides - multicomponent coupling reaction - amide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707229.
  • Supporting Information
 

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