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Stereoselective synthesis of substituted 1,3-dienes from propargylic esters: electrophilic-metal or redox catalysis?

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Abstract

1,3-Diene architectures are not only widely present in natural products, pharmaceuticals, and functional organic materials but also serve as versatile building blocks to furnish important functionalized molecules in synthetic chemistry due to conjugated repeating C=C units. Accordingly, various strategies to access substituted 1,3-dienes in a stereoselective manner have been developed. However, chemo-, regio- and stereoselective synthesis of highly substituted 1,3-dienes still remains elusive and challenging. Readily available propargylic esters have emerged as an appealing class of synthetic intermediates for accessing functionalized 1,3-dienes, especially challenging tri- or tetrasubstituted variants, via transition-metal catalysis, including electrophilic metal and redox neutral catalysis. This review, for the first time, systematically highlights recent advances in transition-metal catalyzed synthesis of substituted 1,3-dienes from propargylic esters, discusses the mechanisms and synthetic utilities, and gives the remaining challenges and potential opportunities in this field.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22071111), the Jiangsu Specially Appointed Professor Plan, the Natural Science Foundation of Jiangsu Province (BK20201368, BK20220409), and the Postgraduate Research & Practice Innovation Program of Jiangsu Province (KYCX23_1683).

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  1. Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210023, China

    Mengfu Dai & Liang-An Chen

  2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, China

    Liangliang Song

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Dai, M., Song, L. & Chen, LA. Stereoselective synthesis of substituted 1,3-dienes from propargylic esters: electrophilic-metal or redox catalysis?. Sci. China Chem. (2024). https://doi.org/10.1007/s11426-023-1925-4

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