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Effective Synthesis of Benzyl 3-Phenylpropiolates Via Copper(I)-Catalyzed Esterification of Alkynoic Acids with Benzyl Halides Under Ligand-Free Conditions

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Abstract

We developed an efficient way to prepare benzyl 3-phenylpropiolates via copper-catalyzed coupling between corresponding benzyl halides and alkynoic acids under ligand-free condition. This methodology is also suitable for aromatic and α,β-unsaturated acids. The desired esters could be obtained in good yields.

Graphical Abstract

We developed an efficient way to prepare benzyl 3-phenylpropiolates via copper-catalyzed coupling between corresponding benzyl halides and alkynoic acids under ligand-free condition. This methodology is also suitable for aromatic and cinnamic acids. The desired esters could be obtained in good yields.

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Acknowledgments

The research is supported by Open Fund (PLN1409) of State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation (Southwest Petroleum University), the Major Program of the National Natural Science Foundation of China (51490653) and 973 Program (2013CB228004). We are grateful to the Grants from the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry and the Key Laboratory of Organic Synthesis of Jiangsu Province.

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Authors and Affiliations

  1. State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu, 610500, People’s Republic of China

    Jincheng Mao, Xiaojiang Yang, Yongming Li & Jinzhou Zhao

  2. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, People’s Republic of China

    Jincheng Mao, Hong Yan & Yue He

Authors
  1. Jincheng Mao
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  2. Xiaojiang Yang
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  3. Hong Yan
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  4. Yue He
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  6. Jinzhou Zhao
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Corresponding author

Correspondence to Jincheng Mao.

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Mao, J., Yang, X., Yan, H. et al. Effective Synthesis of Benzyl 3-Phenylpropiolates Via Copper(I)-Catalyzed Esterification of Alkynoic Acids with Benzyl Halides Under Ligand-Free Conditions. Catal Lett 146, 886–892 (2016). https://doi.org/10.1007/s10562-015-1690-5

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  • DOI: https://doi.org/10.1007/s10562-015-1690-5

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