C−H Functionalization Strategies in Quinone Chemistry

Quinones are a class of redox‐active compounds widely encountered in natural products, pharmaceuticals and materials science. Traditional approaches to quinone derivatisation often rely on pre‐functionalised precursors or harsh reaction conditions, limiting structural diversity and sustainability. C−H functionalisation offers a transformative avenue by directly converting inert C−H bonds into C–X or C–C bonds, thereby streamlining synthetic routes, minimising waste and unlocking novel substitution patterns on the quinone core. Key strategies include transition‐metal catalysis (notably palladium, rhodium and copper), directing‐group assistance for site‐selectivity, photoredox‐promoted processes and base‐mediated radical couplings. These methods enable selective arylation, alkylation, amination and halogenation at positions that were previously inaccessible or required multiple steps of protection and activation. Recent advances have focused on mild and eco-friendly conditions, compatibility with sensitive functional groups and expansion into asymmetric and flow chemistry formats. The ability to tailor redox properties, tune electronic features and introduce complex side chains directly on the quinone scaffold has profound implications for drug discovery, agrochemicals and organic electronics.

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C−H Functionalization Strategies in Quinone Chemistry publication trend

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Technical terms

C−H functionalisation: The direct transformation of a carbon–hydrogen bond into a carbon–heteroatom or carbon–carbon bond without prior functional group manipulation.

Directing group: A substituent temporarily installed on a molecule to guide a catalyst or reagent to a specific C−H bond, enhancing regioselectivity.

Photoredox catalysis: A process using visible‐light to excite a photocatalyst, which then mediates single-electron transfer events to generate reactive radical species.

Redox‐active scaffold: A molecular framework capable of undergoing reversible oxidation and reduction, often central to quinone chemistry.

Radical coupling: A reaction in which two radical intermediates combine to form a new covalent bond, frequently used for C−C bond construction in quinones.

References

1. Diversity-Orientated Synthesis and Biological Properties of Compounds Based on the N-Phenylquinoneimine Scaffold. Molecules (2024).
2. Different metal salts catalyzed alkylation or cycloaddition of indolylquinones with diethyl malonate via base-mediated. Journal of Molecular Structure (2025).
3. Synthesis of Acylated Naphthohydroquinones Through Photo-Friedel–Crafts Acylation and Evaluation of Their Antibiotic Potential. Photochem (2024).