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Updated: May 20, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
An iodocyclization approach to substituted 3-iodothiophenes
Bartolo Gabriele1, Raffaella Mancuso, Giuseppe Salerno
1Dipartimento di Scienze Farmaceutiche, Università della Calabria, 87036 Arcavacata di Rende (CS), Italy. b.gabriele@unical.it
Researchers developed a new method for synthesizing 3-iodothiophenes using direct iodocyclization of alkynylthiol compounds. This efficient process converts readily available precursors into valuable thiophene derivatives in good yields.
Area of Science:
- Organic Chemistry
- Heterocyclic Chemistry
Background:
- Thiophene derivatives are important scaffolds in medicinal chemistry and materials science.
- Efficient synthesis of functionalized thiophenes, particularly iodinated ones, is crucial for further chemical transformations.
Purpose of the Study:
- To present a novel and direct method for synthesizing 3-iodothiophene derivatives.
- To explore the utility of alkynylthiol derivatives in constructing iodinated thiophene rings.
Main Methods:
- Direct iodocyclization of 1-mercapto-3-yn-2-ols using molecular iodine.
- Reaction conditions involved sodium bicarbonate as a base in acetonitrile at room temperature.
Main Results:
- A variety of 3-iodothiophene derivatives were synthesized in good yields.
- The starting 1-mercapto-3-yn-2-ols were readily prepared from alpha-mercapto ketones or esters.
Conclusions:
- The presented iodocyclization offers a straightforward and efficient route to 3-iodothiophenes.
- This method provides access to valuable intermediates for further synthetic elaborations.
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