Iodonium Ylides in Organic Synthesis
Summary
Iodonium ylides are hypervalent iodine–carbon species that have emerged as versatile precursors for carbon-centred reactive intermediates. Characterised by a three-centre, four-electron bond between iodine and the adjacent carbon atom, these ylides can undergo facile homolytic or heterolytic cleavage to generate metal-stabilised carbenoids or free carbenes. Their ability to deliver carbene equivalents under mild, metal-catalysed or photochemical conditions has enabled a broad array of transformations, including cyclopropanation, C–H insertion, ylide rearrangement and heteroatom functionalisation. The intrinsic stability of iodonium ylides can be modulated through electronic tuning of substituents, facilitating selective activation pathways and precise stereochemical control. Recent advances have focused on harnessing halogen-bonding interactions to influence reactivity, developing chiral ligand environments for enantioselective processes and exploiting photochemical activation to access previously elusive bond-forming events. Across pharmaceuticals, agrochemicals and material science, iodonium ylides offer sustainable, high-atom-economy routes for complex molecule construction.
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Iodonium Ylides in Organic Synthesis publication trend
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Technical terms
Iodonium ylide: A hypervalent iodine compound featuring a formal negative charge on carbon, serving as a carbene or radical precursor.
Carbenoid: A metal-stabilised species that behaves similarly to a free carbene in bond-forming reactions.
Halogen bonding: A noncovalent interaction between an electrophilic region on a halogen atom and a nucleophilic site, influencing molecular conformation and reactivity.
Enantioselectivity: The preferential formation of one enantiomer over another in a chiral reaction pathway, expressed as an enantiomeric excess.
Photoirradiation: The use of light energy to promote homolysis or electronic excitation, initiating chemical transformations without thermal input.
References
- Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides. Molecules (2001).
- Synthesis and Properties of ortho-t-BuSO2C6H4-Substituted Iodonium Ylides. Crystals (2021).
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