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Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones

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Abstract

Privileged biaryl frameworks, BINOL and NOBIN, were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions. The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities. This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency. Notably, the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions, providing an effective handle for further enriching the library of BINOLs and NOBINs. Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21825105), the Guangdong Provincial Key Laboratory of Catalysis (2020B121201002), the Guangdong Innovative Program (2019BT02Y335), the Shenzhen Nobel Prize Scientists Laboratory Project (C17213101), and the SUSTech Special Fund for the Construction of High-Level Universities (G02216402). The authors appreciate the assistance of SUSTech Core Research Facilities.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, 150001, China

    Ji-Wei Zhang

  2. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China

    Ji-Wei Zhang, Fei Jiang, Ye-Hui Chen, Shao-Hua Xiang & Bin Tan

  3. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, 518055, China

    Shao-Hua Xiang

Authors
  1. Ji-Wei Zhang
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  2. Fei Jiang
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  4. Shao-Hua Xiang
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  5. Bin Tan
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Correspondence to Bin Tan.

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Conflict of interest The authors declare no conflict of interest.

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Zhang, JW., Jiang, F., Chen, YH. et al. Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones. Sci. China Chem. 64, 1515–1521 (2021). https://doi.org/10.1007/s11426-021-1003-9

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