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A practical access to fluoroalkylthio(seleno)-functionalized bicyclo[1.1.1]pentanes

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Abstract

Rational design of new bioisosteres through introduction of high-value functional groups to bicyclo[1.1.1]pentane (BCP) is of particular use for drug discovery. Disclosed herein is the first access to valuable fluoroalkylthio(seleno)-functionalized BCPs. A range of SCF3, SCF2H, SCFH2, SeCF3, SeC4F9, and SeC8F17 groups are readily incorporated to BCPs under mild conditions. Concomitant installation of a sulfone provides a platform for incorporation of the BCP motif to bioactive molecules. This practical protocol features novel BCP scaffolds, broad substrate scope, excellent atom-economy, simple operation, and gram-scale preparation.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21722205, 21971173), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201905), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

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Authors and Affiliations

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China

    Zhen Wu, Yaohui Xu, Jige Liu, Xinxin Wu & Chen Zhu

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  1. Zhen Wu
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  2. Yaohui Xu
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  3. Jige Liu
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  4. Xinxin Wu
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  5. Chen Zhu
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Correspondence to Chen Zhu.

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Wu, Z., Xu, Y., Liu, J. et al. A practical access to fluoroalkylthio(seleno)-functionalized bicyclo[1.1.1]pentanes. Sci. China Chem. 63, 1025–1029 (2020). https://doi.org/10.1007/s11426-020-9733-y

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  • DOI: https://doi.org/10.1007/s11426-020-9733-y

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