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“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis

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  • Soo Bok Kim

    (Sungkyunkwan University)

  • Dong Hyeon Kim

    (Sungkyunkwan University)

  • Han Yong Bae

    (Sungkyunkwan University)

Abstract

Sulfur(VI) fluoride exchange (SuFEx) has emerged as an innovative click chemistry to harness the pivotal connectivity of sulfonyl fluorides. Synthesizing such alkylated S(VI) molecules through a straightforward process is of paramount importance, and their water-compatibility opens the door to a plethora of applications in biorelevant and materials chemistry. Prior aquatic endeavors have primarily focused on delivering catalysts involving ionic mechanisms, studies regarding visible-light photocatalytic transformation are unprecedented. Herein we report an on-water accelerated dearomative aquaphotocatalysis for heterocyclic alkyl SuFEx hubs. Notably, water exerts a pronounced accelerating effect on the [2 + 2] cycloaddition between (hetero)arylated ethenesulfonyl fluorides and inert heteroaromatics. This phenomenon is likely due to the high-pressure-like reactivity amplification at the water-oil interface. Conventional solvents proved totally ineffective, leading to the isomerization of the starting material.

Suggested Citation

  • Soo Bok Kim & Dong Hyeon Kim & Han Yong Bae, 2024. "“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47861-w
    DOI: 10.1038/s41467-024-47861-w
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    References listed on IDEAS

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    1. Jing-Si Wang & Kai Wu & Changzhen Yin & Kang Li & Yahao Huang & Jia Ruan & Ximin Feng & Peng Hu & Cheng-Yong Su, 2020. "Cage-confined photocatalysis for wide-scope unusually selective [2 + 2] cycloaddition through visible-light triplet sensitization," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
    2. Feng Zhou & Chao-Jun Li, 2014. "The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water," Nature Communications, Nature, vol. 5(1), pages 1-7, September.
    3. Ruting Xu & Tianxiao Xu & Mingcheng Yang & Tianpeng Cao & Saihu Liao, 2019. "A rapid access to aliphatic sulfonyl fluorides," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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