Nickel-Catalyzed Carbonylative Synthesis of β-Ketonitriles from α-Bromonitriles and Arylboronic Acids

A new carbonylation reaction of α-bromonitriles with arylboronic acids has been explored for the synthesis of β-ketonitriles. Notably, the reaction is catalyzed by an inexpensive nickel catalyst and operates under mild reaction conditions without the direct use of gaseous CO. It demonstrates a general and complementary carbonylation route for the synthesis of valuable β-ketonitrile products, and a variety of products were obtained in moderate to high yields with good functional group tolerance. Moreover, the synthetic utility of this method is evidenced by a scale-up experiment and subsequent functionalization of the resulting β-ketonitriles.

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Journal
Organic Letters
Published
2026-05-08
DOI
https://doi.org/10.1021/acs.orglett.6c01685
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Nickel-Catalyzed Carbonylative Synthesis of β-Ketonitriles from α-Bromonitriles and Arylboronic Acids

Jiacong Ma, Zilin Huang, Yuting Jiang, Xinxin Qi et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Nickel-Catalyzed Carbonylative Synthesis of β-Ketonitriles from α-Bromonitriles and Arylboronic Acids

Jiacong Ma, Zilin Huang, Yuting Jiang, Xinxin Qi, Xiao-Feng Wu
article en

Abstract

A new carbonylation reaction of α-bromonitriles with arylboronic acids has been explored for the synthesis of β-ketonitriles. Notably, the reaction is catalyzed by an inexpensive nickel catalyst and operates under mild reaction conditions without the direct use of gaseous CO. It demonstrates a general and complementary carbonylation route for the synthesis of valuable β-ketonitrile products, and a variety of products were obtained in moderate to high yields with good functional group tolerance. Moreover, the synthetic utility of this method is evidenced by a scale-up experiment and subsequent functionalization of the resulting β-ketonitriles.

Organic Letters
Zhejiang Sci-Tech University (CN), Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Leibniz Institute for Catalysis (DE), Ingenierie des Materiaux polymeres (FR), Dalian National Laboratory for Clean Energy (CN), Interface (United Kingdom) (GB)
National Natural Science Foundation of China, Chinese Academy of Sciences, National Key Research and Development Program of China
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
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