Skeletal Editing: Interconversion of Arenes and Heteroarenes

Skeletal editing involves making specific point‐changes to the core of a molecule through the selective insertion, deletion or exchange of atoms. It thus represents a potentially powerful strategy for the step‐economic modification of complex substrates and is a perfect complement to methods such as...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 106; no. 3
Main Authors Joynson, Ben W., Ball, Liam T.
Format Journal Article
LanguageEnglish
Published Zürich Wiley Subscription Services, Inc 01.03.2023
Subjects
Aromatic compounds
atom deletion
atom exchange
atom insertion
Bioactive compounds
Biological activity
drug design
drug discovery
Editing
Heterocyclic compounds
insertion
molecular editing
skeletal editing
Substrates
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Summary:Skeletal editing involves making specific point‐changes to the core of a molecule through the selective insertion, deletion or exchange of atoms. It thus represents a potentially powerful strategy for the step‐economic modification of complex substrates and is a perfect complement to methods such as C−H functionalization that target the molecular periphery. Given their ubiquity in biologically active compounds, the ability to perform skeletal editing on – and therefore interconvert between – aromatic heterocycles is especially valuable. This review summarizes both recent and key historical examples of skeletal editing as applied to interconversion of aromatic rings; we anticipate that it will serve to highlight not only the innovative and enabling nature of current skeletal editing methods, but also the tremendous opportunities that still exist in the field.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202200182