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Highly active and efficient catalysts for alkoxycarbonylation of alkenes

Author

Listed:
  • Kaiwu Dong

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Xianjie Fang

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Samet Gülak

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Robert Franke

    (Evonik Performance Materials GmbH
    Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum)

  • Anke Spannenberg

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Helfried Neumann

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Ralf Jackstell

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

  • Matthias Beller

    (Leibniz-Institut für Katalyse e.V. an der Universität Rostock)

Abstract

Carbonylation reactions of alkenes constitute the most important industrial processes in homogeneous catalysis. Despite the tremendous progress in this transformation, the development of advanced catalyst systems to improve their activity and widen the range of feedstocks continues to be essential for new practical applications. Herein a palladium catalyst based on 1,2-bis((tert-butyl(pyridin-2-yl)phosphanyl)methyl)benzene L3 (pytbpx) is rationally designed and synthesized. Application of this system allows a general alkoxycarbonylation of sterically hindered and demanding olefins including all kinds of tetra-, tri- and 1,1-disubstituted alkenes as well as natural products and pharmaceuticals to the desired esters in excellent yield. Industrially relevant bulk ethylene is functionalized with high activity (TON: >1,425,000; TOF: 44,000 h−1 for initial 18 h) and selectivity (>99%). Given its generality and efficiency, we expect this catalytic system to immediately impact both the chemical industry and research laboratories by providing a practical synthetic tool for the transformation of nearly any alkene into a versatile ester product.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14117
    DOI: 10.1038/ncomms14117
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    Cited by:

    1. 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.
    2. Fei Wu & Bo Wang & Na-Qi Li & Hui-Yi Yang & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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