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Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

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Abstract

Here, we describe a strategy for the copper-catalyzed asymmetric heteroarylation of yne-thiophene carbonates with indoles via remote substitution. The key to the success of this strategy lies in the design of the alkynyl group at the ortho-position of the heterocycle thiophene, enabling the formation of a triarylmethane moiety via very remote substitution. Thus, the concept of remote copper-catalyzed asymmetric transformation extends not only to yne-allylic esters but also to yne-aryl esters. The reaction readily provides a diverse array of chiral triarylmethanes with high efficiency, enantioselectivity, and excellent functional group compatibility. Moreover, facile follow-up transformations underscore their potential utility in the synthesis of various enantioenriched building blocks. Preliminary mechanistic studies support the plausibility of the remote substitution pathway.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21801087, 22201089).

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Authors and Affiliations

  1. CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology of Ministry of Education, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan, 430079, China

    Hao-Dong Qian, Xiang Li, Tingrui Yin, Wei-Feng Qian, Chunhui Zhao, Cuiju Zhu & Hao Xu

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  1. Hao-Dong Qian
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  2. Xiang Li
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  3. Tingrui Yin
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  4. Wei-Feng Qian
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  7. Hao Xu
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Correspondence to Cuiju Zhu or Hao Xu.

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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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Qian, HD., Li, X., Yin, T. et al. Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates. Sci. China Chem. 67, 1175–1180 (2024). https://doi.org/10.1007/s11426-023-1922-5

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  • DOI: https://doi.org/10.1007/s11426-023-1922-5

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