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Perfluoropyridylation of indoles via reaction of perfluorinated pyridines with indole compounds

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Abstract

The reaction of perfluoropyridines with indoles and bis(indolyl)methanes (BIMs) was investigated. The aromatic nucleophilic substitution of pentafluoropyridine with indoles occurs at the 4-position of pyridine ring by nitrogen site of indolyl anion, while reaction with 2,3,5,6-tetrafluoro-4-(phenylsulfonyl)pyridine gave a mixture of products arising substitution at 2-position of pyridine ring and replacement of phenylsulfonyl group. Furthermore, the reaction of pentafluoropyridine with BIMs yielded mixture of mono- and bis-perfluoropyridyl products.

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Acknowledgements

The authors wish to thank Vali-e-Asr University of Rafsanjan for partially funding this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, 77176, Islamic Republic of Iran

    Tahereh Moradi, Reza Ranjbar-Karimi, Alireza Poorfreidoni & Hossein Mehrabi

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  1. Tahereh Moradi
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  2. Reza Ranjbar-Karimi
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  3. Alireza Poorfreidoni
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  4. Hossein Mehrabi
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Correspondence to Reza Ranjbar-Karimi.

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Moradi, T., Ranjbar-Karimi, R., Poorfreidoni, A. et al. Perfluoropyridylation of indoles via reaction of perfluorinated pyridines with indole compounds. J IRAN CHEM SOC 17, 1347–1357 (2020). https://doi.org/10.1007/s13738-020-01858-6

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  • DOI: https://doi.org/10.1007/s13738-020-01858-6

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