# Iron-Catalyzed Thioarylation of Arenes Using Saccharin-Derived Reagents

**Authors:** Lachlan
J. N. Waddell, Oluwajuwon A. M. Okunade, Amy C. Dodds, Michael C. H. Lok, R. Nisha Khanizeman, Andrew Sutherland

PMC · DOI: 10.1021/acs.joc.5c00250 · The Journal of Organic Chemistry · 2025-04-17

## TL;DR

A new method uses iron and saccharin-based reagents to efficiently create biaryl sulfides under mild conditions.

## Contribution

A novel iron-catalyzed thioarylation method using saccharin-derived reagents for mild and efficient synthesis of biaryl sulfides.

## Key findings

- The method enables rapid synthesis of unsymmetrical biaryl sulfides under mild conditions.
- It works efficiently with electron-deficient thioaryl species previously difficult to functionalize.
- The approach allows functionalization of bioactive compounds without harsh conditions.

## Abstract

Biaryl sulfides are
important scaffolds found in various natural
products and pharmaceutically active compounds. One of the main approaches
for the synthesis of this compound class involves the substitution
of arenes using electrophilic thioaryl species. However, these methods
generally require acidic activation of the electrophile, more forcing
conditions, and long reaction times. Here, we describe the combination
of the super Lewis acid iron(III) triflimide with saccharin-based
thioarylation reagents for the rapid synthesis of unsymmetrical biaryl
sulfides under mild conditions. This approach was effective with electron-deficient
thioaryl species that performed poorly with previous methods, allowing
the efficient functionalization of bioactive compounds.

## Linked entities

- **Chemicals:** saccharin (PubChem CID 5143)

## Full-text entities

- **Chemicals:** Iron (MESH:D007501), Arenes (-), Saccharin (MESH:D012439)

## Full text

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## Figures

4 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12038848/full.md

## References

29 references — full list in the complete paper: https://tomesphere.com/paper/PMC12038848/full.md

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Source: https://tomesphere.com/paper/PMC12038848