“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis

Soo Bok Kim, Dong Hyeon Kim and Han Yong Bae ()
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Soo Bok Kim: Sungkyunkwan University
Dong Hyeon Kim: Sungkyunkwan University
Han Yong Bae: Sungkyunkwan University

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-47861-w

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