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Nickel-catalyzed carbonylative four-component 1,4-dicarbofunctionalization of 1,3-enynes

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Abstract

An efficient Ni-catalyzed four-component 1,4-carbocarbonylation of 1,3-enynes with activated alkyl halides and arylboronic acids under atmospheric pressure of CO is presented. By tuning the electronic and steric effects of alkyl radicals, both electron-rich and electron-deficient 1,3-enynes were compatible with this cascade. This protocol features mild conditions, broad substrate scope, excellent functional group compatibility and facile gram-scale synthesis, providing a practical approach to the quaternary carbon center-containing allenyl ketones. Mechanistic study revealed that the acyl-NiII species plays an important role in both the coupling and the alkyl radical generation processes.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22171220, 21971201) and the Fundamental Research Funds of the Central Universities (xtr072022003). We also thank Mr Zhang, Miss Feng and Miss Bai at the Instrument Analysis Center of Xi’an Jiaotong University for their assistance with NMR and HRMS analysis.

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Authors and Affiliations

  1. Department of Chemistry, School of Chemistry, Xi’an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage, Materials and Devices, Ministry of Education, Xi’an Jiaotong University, Xi’an, 710049, China

    Yan Zhao, Qi-Chao Shan, Hong Xin, Pin Gao, Xin-Hua Duan & Li-Na Guo

  2. School of Electrical Engineering, Xi’an Jiaotong University, Xi’an, 710049, China

    Xu Yang

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  1. Yan Zhao
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  2. Qi-Chao Shan
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  3. Hong Xin
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  5. Xu Yang
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  6. Xin-Hua Duan
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  7. Li-Na Guo
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Correspondence to Li-Na Guo.

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Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Zhao, Y., Shan, QC., Xin, H. et al. Nickel-catalyzed carbonylative four-component 1,4-dicarbofunctionalization of 1,3-enynes. Sci. China Chem. (2024). https://doi.org/10.1007/s11426-024-1973-2

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  • DOI: https://doi.org/10.1007/s11426-024-1973-2

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