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Recyclable Copper-Catalyzed Decarboxylative C–C Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids

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Abstract

A highly efficient heterogeneous copper(I)-catalyzed decarboxylative C–C coupling of α-amino acids with various carbon nucleophiles has been developed that proceeds smoothly in toluene at 110 °C by using an 2-aminoethylamino-modified SBA-15-supported copper(I) bromide complex as the catalyst and di-tert-butyl peroxide as the oxidant and provides a novel and practical approach for the synthesis of diverse propargylamines, indolyl pyrrolidines and piperidines, and β-nitroamines in good yields. The new heterogeneous copper(I) catalyst can be facilely prepared from commercially easily available and inexpensive reagents via a simple procedure, and exhibits a slightly higher catalytic activity than homogeneous CuBr/TMEDA system and can be recycled at least 8 times without any apparent loss of catalytic efficiency.

Graphical Abstract

A recyclable copper(I)-catalyzed decarboxylative C–C coupling of α-amino acids with various carbon nucleophiles has been developed by using an SBA-15-supported copper(I) bromide complex as the catalyst, providing a novel and practical approach for the synthesis of diverse propargylamines, indolyl pyrrolidines and piperidines, and β-nitroamines.

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Acknowledgements

We thank the National Natural Science Foundation of China (No. 21664008) for financial support.

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Authors and Affiliations

  1. College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, China

    Ruonan Zhao, Bin Huang & Mingzhong Cai

  2. School of Biology and Environmental Engineering, Jingdezhen University, Jingdezhen, 333000, China

    Jianying Li

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  1. Ruonan Zhao
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  2. Jianying Li
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  3. Bin Huang
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Correspondence to Bin Huang or Mingzhong Cai.

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Zhao, R., Li, J., Huang, B. et al. Recyclable Copper-Catalyzed Decarboxylative C–C Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids. Catal Lett 153, 178–187 (2023). https://doi.org/10.1007/s10562-022-03936-1

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