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Identification of a potent palladium-aryldiphosphine catalytic system for high-performance carbonylation of alkenes

Author

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  • Kang Zhao

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Hongli Wang

    (Chinese Academy of Sciences)

  • Teng Li

    (Chinese Academy of Sciences)

  • Shujuan Liu

    (Chinese Academy of Sciences)

  • Enrico Benassi

    (Novosibirsk State University)

  • Xiao Li

    (Nanjing Chengzhi Clean Energy Co., LTD.)

  • Yao Yao

    (Nanjing Chengzhi Clean Energy Co., LTD.)

  • Xiaojun Wang

    (Nanjing Chengzhi Clean Energy Co., LTD.)

  • Xinjiang Cui

    (Chinese Academy of Sciences)

  • Feng Shi

    (Chinese Academy of Sciences)

Abstract

The development of stable and efficient ligands is of vital significance to enhance the catalytic performance of carbonylation reactions of alkenes. Herein, an aryldiphosphine ligand (L11) bearing the [Ph2P(ortho-C6H4)]2CH2 skeleton is reported for palladium-catalyzed regioselective carbonylation of alkenes. Compared with the industrially successful Pd/1,2-bis(di-tert-butylphosphinomethyl)benzene catalyst, catalytic efficiency catalyzed by Pd/L11 on methoxycarbonylation of ethylene is obtained, exhibiting better catalytic performance (TON: >2,390,000; TOF: 100,000 h−1; selectivity: >99%) and stronger oxygen-resistance stability. Moreover, a substrate compatibility (122 examples) including chiral and bioactive alkenes or alcohols is achieved with up to 99% yield and 99% regioselectivity. Experimental and computational investigations show that the appropriate bite angle of aryldiphosphine ligand and the favorable interaction of 1,4-dioxane with Pd/L11 synergistically contribute to high activity and selectivity while the electron deficient phosphines originated from electron delocalization endow L11 with excellent oxygen-resistance stability.

Suggested Citation

  • Kang Zhao & Hongli Wang & Teng Li & Shujuan Liu & Enrico Benassi & Xiao Li & Yao Yao & Xiaojun Wang & Xinjiang Cui & Feng Shi, 2024. "Identification of a potent palladium-aryldiphosphine catalytic system for high-performance carbonylation of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46286-9
    DOI: 10.1038/s41467-024-46286-9
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    References listed on IDEAS

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    4. Kaiwu Dong & Xianjie Fang & Samet Gülak & Robert Franke & Anke Spannenberg & Helfried Neumann & Ralf Jackstell & Matthias Beller, 2017. "Highly active and efficient catalysts for alkoxycarbonylation of alkenes," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
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