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

BACKGROUND

Bicyclo[1.1.1]pentanes (BCPs), recognized as bioisosteres for paradisubstituted 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-, cyanosubstituted 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.