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Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations

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Abstract

Pentafluorosulfanylated (SF5-) aromatics have shown great potential in drugs, and the bioisosteric replacement of aromatic ring with bicyclo[1.1.1]pentane (BCP) unit has attracted considerable attention recently. Consequently, pentafluorosulfanylated bicyclo[1.1.1]pentanes (SF5-BCPs) should have application in the realm of drug discovery. In this study, a one-pot iodopentafluorosulfanylation of [1.1.1]propellane with SF5Cl and CH2I2 for the practical synthesis of iodopentafluorosulfanylated bicyclo[1.1.1]pentane (SF5-BCP-I) was developed. SF5-BCP-I was the first example of SF5-BCPs that could be transformed. The first general method to access SF5-substituted bicyclo[1.1.1]pentane derivatives was demonstrated through photoredox-catalyzed radical addition of SF5-BCP-I to alkenes and alkynes.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21991121) and the National Key Research and Development Program of China (2021YFF0701700).

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Authors and Affiliations

  1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China

    Xin Zhao, Jia-Yi Shou & Feng-Ling Qing

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  1. Xin Zhao
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  2. Jia-Yi Shou
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  3. Feng-Ling Qing
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Correspondence to Feng-Ling Qing.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://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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Zhao, X., Shou, JY. & Qing, FL. Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations. Sci. China Chem. 66, 2871–2877 (2023). https://doi.org/10.1007/s11426-023-1715-2

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