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"On-Water" accelerated dearomative cycloaddition via aquaphotocatalysis.
Soo Bok Kim1, Dong Hyeon Kim1, Han Yong Bae2
1Department of Chemistry, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Nature Communications
|May 8, 2024
Summary
This study introduces an innovative water-accelerated photocatalysis for creating sulfur(VI) fluoride exchange (SuFEx) molecules. This new method efficiently synthesizes complex heterocyclic compounds, expanding possibilities in materials and biorelevant chemistry.
Area of Science:
- Organic Chemistry
- Click Chemistry
- Photocatalysis
Background:
- Sulfur(VI) fluoride exchange (SuFEx) is a key click chemistry reaction utilizing sulfonyl fluorides.
- Water-compatible SuFEx compounds are crucial for biorelevant and materials science applications.
- Existing aquatic SuFEx methods often rely on ionic mechanisms, with limited exploration of photocatalysis.
Purpose of the Study:
- To develop a novel on-water visible-light photocatalytic method for synthesizing alkylated S(VI) molecules.
- To investigate the accelerating effect of water on SuFEx reactions involving heterocyclic compounds.
- To establish a straightforward and efficient route to heterocyclic alkyl SuFEx hubs.
Main Methods:
- Dearomative aquaphotocatalysis employing visible light.
- Utilizing (hetero)arylated ethenesulfonyl fluorides and inert heteroaromatics as substrates.
- Conducting reactions at the water-oil interface to study reactivity amplification.
Main Results:
- Demonstrated an accelerated [2+2] cycloaddition reaction for SuFEx hub synthesis in water.
- Observed a significant acceleration effect of water, attributed to interfacial reactivity amplification.
- Found conventional solvents to be ineffective, leading to starting material isomerization.
Conclusions:
- Developed a pioneering on-water photocatalytic approach for SuFEx chemistry.
- Highlighted the unique accelerating role of water in this specific cycloaddition reaction.
- Established a new, efficient pathway for synthesizing water-compatible heterocyclic SuFEx compounds.
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