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-, cy-ano-substituted BCPs from sulfonyl cyanide and [1.1.1]propellane. In this study, the synthet-ic schemes were designed to show the chemical reactions. Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS) were used to identify and characterize the final com-pounds.

Results: This method does not require photocatalysts, metals, or light, generating BCP ni-triles 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.

Keywords: Pentanes, bioisosteres, sulfonyl cyanide