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Asymmetric synthesis of binaphthyls through photocatalytic cross-coupling and organocatalytic kinetic resolution

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Abstract

By capitalizing on the capability of photoredox catalysis to generate reactive radical intermediate under mild conditions, we established a photocatalytic cross-coupling protocol that could deliver both derivatives from 1-bromo-2-naphthols in combination with 2-naphthols or 2-naphthylamines. This distinct activation mode could overcome structural or electronic limitation associated with conventional coupling pathways. Additionally, a novel kinetic resolution protocol of unprotected BINOLs has been established with azodicarboxylates via chiral phosphoric acid (CPA) catalysis. Selectivity factor of up to 175 could be achieved and delivered to both enantiomers in atropisomerically enriched form after a simple work-up.

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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 Special Funds (JCYJ20190812-112603598, JCYJ20210324120205016), the Shenzhen Nobel Prize Scientists Laboratory Project (C17213101) and the SUSTech Special Fund for the Construction of High-Level Universities (G02216302). 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

    Heng-Hui Li

  2. Shenzhen Grubbs Institute, Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China

    Heng-Hui Li, Jia-Yan Zhang, Shaoyu Li, Yong-Bin Wang, Jun Kee Cheng, Shao-Hua Xiang & Bin Tan

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

    Shao-Hua Xiang

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  1. Heng-Hui Li
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Li, HH., Zhang, JY., Li, S. et al. Asymmetric synthesis of binaphthyls through photocatalytic cross-coupling and organocatalytic kinetic resolution. Sci. China Chem. 65, 1142–1148 (2022). https://doi.org/10.1007/s11426-022-1246-8

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