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.