# Thioglycoside functionalization via chemoselective phosphine acceleration of a photocatalytic thiol–ene reaction

**Authors:** Arun K. Thangarasu, Charlie Fehl

PMC · DOI: 10.1039/d5cc00131e · Chemical Communications (Cambridge, England) · 2025-04-29

## TL;DR

This paper introduces a new method to create thioglycosides using mild light-driven reactions in water, making the process more efficient and environmentally friendly.

## Contribution

The use of phosphines as a photoredox mediator to enable mild thioglycoside synthesis in water is novel.

## Key findings

- Phosphines accelerate radical thiol–ene reactions under visible light and ambient conditions.
- The method allows for chemoselective thioglycoside synthesis in fully aqueous environments.
- The process is operationally simple and environmentally friendly.

## Abstract

Thioglycosides are enzymatically stable carbohydrate variants used in biotechnology as probes and investigational drugs. To date, harsh activation conditions limit the scope of thiol–ene sugar ligations. Here, we show that phosphines act as a photoredox mediator to accelerate radical thiol–ene reactions between thiosugars and olefins, enabling mild visible light-driven, ambient, and fully aqueous conditions.

Green, operationally simple, and chemoselective access to thioglycoside analogs using mild photoredox condition in water.

## Full-text entities

- **Chemicals:** olefins (MESH:D000475), Thioglycoside (MESH:D013865), thiosugars (MESH:D054330), phosphines (MESH:D010720), photoredox (-), phosphine (MESH:C044646), carbohydrate (MESH:D002241)

## Full text

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## Figures

8 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12128037/full.md

## References

32 references — full list in the complete paper: https://tomesphere.com/paper/PMC12128037/full.md

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Source: https://tomesphere.com/paper/PMC12128037