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Significance Bioisoteric replacements for aromatic rings to improve medicinal properties are in high demand. This work presents a comprehensive analysis of heretofore-inaccessible 1,2-difunctionalized bicyclo[1.1.1]pentanes from both chemical and biological vantage points. This analysis will aid those in drug discovery regarding when the application of such systems makes sense and how to access them in such circumstances.

1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long–sought-after mimetics for ortho / meta -substituted arenes