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image of Metal- and Photocatalyst-Free Sulfonylcyanation of [1.1.1]Propellane with Sulfonyl Cyanide

Abstract

Background

Bicyclo[1.1.1]pentanes (BCPs), recognized as bioisosteres for para-disubstituted benzene rings, have gained prominence as valuable bioactive scaffolds in drug research.

Methods

This study describes a radical-coupling method for the synthesis of sulfonyl-, cyano-substituted BCPs from sulfonyl cyanide and [1.1.1]propellane. In this study, the synthetic schemes were designed to show the chemical reactions. Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS) were used to identify and characterize the final compounds.

Results

This method does not require photocatalysts, metals, or light, generating BCP nitriles as a useful building block. The synthetic potential of this mild protocol was showcased by the diverse transformations.

Conclusion

This versatile method significantly expands the range of BCP-type bioisosteres that can be generated.

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2024-11-14
2025-03-01
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  • Article Type:
    Research Article
Keywords: Pentanes ; bioisosteres ; sulfonyl cyanide
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