Skeletal Editing: Interconversion of Arenes and Heteroarenes

Joynson, Ben W.; Ball, Liam T.

Abstract

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.

Citation

Joynson, B. W., & Ball, L. T. (2023). Skeletal Editing: Interconversion of Arenes and Heteroarenes. Helvetica Chimica Acta, 106(3), Article e202200182. https://doi.org/10.1002/hlca.202200182

• Journal Article Type: Review
• Acceptance Date: Jan 13, 2023
• Online Publication Date: Jan 13, 2023
• Publication Date: 2023-03
• Deposit Date: Jan 23, 2023
• Publicly Available Date: Jan 14, 2024
• Journal: Helvetica Chimica Acta
• Print ISSN: 0018-019X
• Electronic ISSN: 1522-2675
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 106
• Issue: 3
• Article Number: e202200182
• DOI: https://doi.org/10.1002/hlca.202200182
• Keywords: Inorganic Chemistry; Organic Chemistry; Physical and Theoretical Chemistry; Drug Discovery; Biochemistry; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/16494607
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/hlca.202200182