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Updated: Jan 20, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Cyclic Vinyl(aryl)iodonium Salts: Synthesis and Reactivity
Konrad Kepski1, Craig R Rice1, Wesley J Moran1
1Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, U.K.
Researchers developed a straightforward method to synthesize cyclic vinyl(aryl)iodonium salts from β-iodostyrenes. These compounds serve as versatile precursors for creating functionalized arylacetylenes and undergoing nucleophilic substitution reactions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Cyclic vinyl(aryl)iodonium salts are valuable synthetic intermediates.
- Efficient synthesis routes for these compounds are crucial for further chemical transformations.
Purpose of the Study:
- To present a convenient and highly regioselective synthesis of five-membered cyclic vinyl(aryl)iodonium salts.
- To explore the reactivity of these novel iodane compounds.
Main Methods:
- Direct synthesis from β-iodostyrenes.
- X-ray crystallography for structural confirmation.
- Reactions with mild base and nonbasic nucleophiles.
Main Results:
- Successful synthesis of five-membered cyclic vinyl(aryl)iodonium salts.
- Confirmation of the heterocyclic structure via X-ray crystallography.
- Rapid conversion to functionalized arylacetylenes.
- Demonstration of SNV reactions with nucleophiles.
Conclusions:
- A facile and regioselective synthetic route to cyclic vinyl(aryl)iodonium salts has been established.
- These λ3-iodanes are versatile building blocks for synthesizing functionalized arylacetylenes.
- The compounds exhibit diverse reactivity, enabling further synthetic applications.
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