Highly active and efficient catalysts for alkoxycarbonylation of alkenes

Kaiwu Dong, Xianjie Fang, Samet Gülak, Robert Franke, Anke Spannenberg, Helfried Neumann, Ralf Jackstell and Matthias Beller ()
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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
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

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: 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.

Date: 2017
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DOI: 10.1038/ncomms14117

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