Citation: Zijun Huang, Jia Tang, Xiongwei Jiang, Tianle Xie, Minmin Zhang, Donghui Lan, Shaofeng Pi, Zhengde Tan, Bing Yi, Yuehui Li. Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α, β-unsaturated amides[J]. Chinese Chemical Letters, ;2022, 33(11): 4842-4845. doi: 10.1016/j.cclet.2022.01.080 shu

Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α, β-unsaturated amides

Zijun Huang ^{a, b, *,} ,
Jia Tang ^a ,
Xiongwei Jiang ^a ,
Tianle Xie ^a ,
Minmin Zhang ^a ,
Donghui Lan ^a ,
Shaofeng Pi ^a ,
Zhengde Tan ^a ,
Bing Yi ^{a, *,} ,
Yuehui Li ^{b, *,}

a.
Hunan Province Key Laboratory of Environmental Catalysis and Waste Rechemistry, College of Materials and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104, China
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China

huangzijun@hnie.edu.cn

bingyi2004@126.com

yhli@licp.cas.cn

Received Date: 24 October 2021
Revised Date: 26 January 2022
Accepted Date: 27 January 2022
Available Online: 3 February 2022

Figures(6)

α, β-Unsaturated primary amides are important intermediates and building blocks in organic synthesis. Herein, we report a ligand-free iron-catalyzed hydroaminocarbonylation of alkynes using NH₄HCO₃ as the ammonia source, enabling the highly efficient and regioselective synthesis of linear α, β-unsaturated primary amides. Various aromatic and aliphatic alkynes are transformed into the desired linear α, β-unsaturated primary amides in good to excellent yields. Further studies show that using NH₄HCO₃ as the ammonia source is key to obtain good yields and selectivity. The utility of this route is demonstrated with the synthesis of linear α, β-unsaturated amides including vanilloid receptor-1 antagonist TRPV-1.
- Iron-catalyzed,
- Alkynes,
- Ammonium bicarbonate,
- Aminocarbonylation,
- Linear α, β-unsaturated amides
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