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Catalyst-controlled regiodivergent 1,2-difunctionalization of alkenes with two carbon-based electrophiles

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Abstract

Regiodivergent catalysis provides an efficient strategic approach for the construction of architecturally different molecules from the same starting materials. In this field, the intermolecular regiodivergent 1,2-difunctionalization of alkenes with two electrophiles is still a challenging task. A ligand-controlled, nickel-catalyzed regiodivergent dicarbofunctionalization of alkenes using both aryl/vinyl halides and acetals as electrophiles under mild reductive reaction conditions has been accomplished. This study provides a general approach to accessing both β-methoxyl esters and γ-methoxyl esters from readily available acrylates, aryl halides and acetals. Experimental mechanistic evidence supports that the difference in regioselective outcomes is attributed to the ligand tuning the reactivity of the nickel catalyst, which results in different catalytic cycles operating for these two reaction conditions.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21871211, 21774029, 22122107) and the Fundamental Research Funds for Central Universities (2042019kf0208).

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Institute for Advanced Studies, Wuhan University, Wuhan, 430072, China

    Md. Belal, Zheqi Li & Guoyin Yin

  2. Institute of Biomedical Materials Industry Technology, Hubei Engineering University, Wuhan, 430074, China

    Lei Zhu

Authors
  1. Md. Belal
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  2. Zheqi Li
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  3. Lei Zhu
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  4. Guoyin Yin
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Corresponding authors

Correspondence to Lei Zhu or Guoyin Yin.

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The authors declare no conflict of interest.

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The supporting information is available online at http://chem.scichina.com and http://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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Belal, M., Li, Z., Zhu, L. et al. Catalyst-controlled regiodivergent 1,2-difunctionalization of alkenes with two carbon-based electrophiles. Sci. China Chem. 65, 514–520 (2022). https://doi.org/10.1007/s11426-021-1172-x

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  • DOI: https://doi.org/10.1007/s11426-021-1172-x

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