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Copper(II)-Catalyzed 1,6-Hydroboration Reactions of p‑Quinone Methides Under Ligand-Free Conditions: A Sequential Methodology to gem-Disubstituted Methanols

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Abstract

The Cu(II) catalyzed 1,6-hydroboration reactions of para-quinone methides with B2pin2 was herein reported. The desired products were all obtained in good to excellent yields under mild conditions. Notably, the reaction extended quite broad substrate scope and showed very good functional group compatibilities. This newly developed strategy has provided an efficient pathway for the construction of C-B bonds via 1,6-hydroboration process.

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Acknowledgements

The authors acknowledge the financial support from the National Natural Science Foundation of China (Nos. 21774029, 22108065), Hubei University Excellent Young and Middle-aged Science and Technology Innovation Team Project (No. T201816), the Natural Science Foundation of Hubei Province of China (No. 2019CFB354), the Opening Fund of Hubei Key Laboratory of Processing and Application of Catalytic materials, Huanggang Normal University (No. 202023404).

Funding

This work was supported by Hubei University Excellent Young and Middle-aged Science and Technology Innovation Team Project, T201816, National Natural Science Foundation of China, 21774029, 22108065, Natural Science Foundation of Hubei Province of China, 2019CFB354, Opening Fund of Hubei Key Laboratory of Processing and Application of Catalytic materials, Huanggang Normal University, 202023404

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Authors and Affiliations

  1. School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, 432000, China

    Weishuang Li, Wei Wen, Shuhan Chen, Bianyang He, Yaoyao Zhang, Bojie Li & Lei Zhu

  2. School of Materials Science and Engineering, Hubei University, Wuhan, 430062, China

    Wei Wen, Shuhan Chen & Lei Zhu

  3. School of Materials Engineering, Yancheng Institute of Technology, Yancheng, 224051, China

    Liang Ding

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  1. Weishuang Li
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  2. Wei Wen
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  3. Shuhan Chen
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  4. Liang Ding
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  5. Bianyang He
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  6. Yaoyao Zhang
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  7. Bojie Li
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  8. Lei Zhu
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Contributions

LZ conceived and designed the experiments; WL, WW and SC performed the experiments. LD and BH helped with characterizing some new compounds; YZ and BL contributed reagents/materials/ analysis tools; LZ reviewed and modified the manuscript.

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Correspondence to Liang Ding, Bianyang He or Lei Zhu.

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Li, W., Wen, W., Chen, S. et al. Copper(II)-Catalyzed 1,6-Hydroboration Reactions of p‑Quinone Methides Under Ligand-Free Conditions: A Sequential Methodology to gem-Disubstituted Methanols. Catal Lett 153, 1294–1299 (2023). https://doi.org/10.1007/s10562-022-04063-7

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  • DOI: https://doi.org/10.1007/s10562-022-04063-7

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