Diaryliodonium Salt Chemistry in Organic Synthesis
Summary
Diaryliodonium salts, characterised by a hypervalent iodine centre bound to two aryl groups, have emerged as versatile electrophilic reagents for the selective transfer of aromatic moieties. Their bench stability and tunable reactivity allow metal-free and metal-catalysed arylation of a broad range of nucleophiles, including oxygen, nitrogen, carbon and sulfur centres. By exploiting ligand and counter-anion effects, chemists achieve high regio- and chemoselectivity under mild conditions, enabling late-stage functionalisation of complex molecules. The retained iodo substituent on the product serves as a strategic handle for further cross-coupling or cyclisation steps, enhancing synthetic efficiency and modularity. Beyond academic interest, these transformations find application in the synthesis of pharmaceuticals, agrochemicals and advanced materials, where atom economy and operational simplicity are paramount.
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Diaryliodonium Salt Chemistry in Organic Synthesis publication trend
The graph below shows the total number of articles in diaryliodonium salt chemistry in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Diaryliodonium salt: A hypervalent iodine(III) compound bearing two aryl ligands, used as an electrophilic aryl-transfer reagent.
Hypervalent iodine: An iodine centre formally exceeding the octet rule, often in oxidation state +3 or +5, that acts as a powerful oxidant or group-transfer agent.
Electrophilic arylation: A reaction in which an electron-rich nucleophile attacks an aryl donor, forming a new C–X or C–C bond.
Nucleophile: A species with a lone pair of electrons or π-bond that attacks an electron-deficient centre, forming a covalent bond.
Atom economy: A measure of how well a reaction incorporates all atoms of the starting materials into the desired product.
Late-stage functionalisation: The selective modification of a complex molecule at a late point in a synthetic sequence to introduce new functionality or diversity.
References
- Transition‐Metal‐Free Difunctionalization of Sulfur Nucleophiles**. Angewandte Chemie International Edition (2023).
- Transition-Metal-Free C‑Diarylations to Reach All-Carbon Quaternary Centers. JACS Au (2024).
- Diarylation of N- and O-nucleophiles through a metal-free cascade reaction. Chem (2022).
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