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Synthesis of sulfonyl chlorides from aryldiazonium salts mediated by a heterogeneous potassium poly(heptazine imide) photocatalyst

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Markushyna,  Yevheniia       
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Antonietti,  Markus       
Markus Antonietti, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Savateev,  Aleksandr       
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Markushyna, Y., Antonietti, M., & Savateev, A. (2022). Synthesis of sulfonyl chlorides from aryldiazonium salts mediated by a heterogeneous potassium poly(heptazine imide) photocatalyst. ACS Organic & Inorganic Au, 2(2), 153-158. doi:10.1021/acsorginorgau.1c00038.


Cite as: https://hdl.handle.net/21.11116/0000-000C-7417-8
Abstract
Visible light photocatalysis is a tool in synthetic chemistry that allows us to utilize the energy of photons via photoinduced electron transfer to promote diverse organic reactions. Herein, a heterogeneous transition metal-free material, a type of carbon nitride photocatalyst, potassium poly(heptazine imide), is employed to produce sulfonyl chlorides from arenediazonium salts under mild conditions (visible light irradiation, room temperature) with 50–95% yields. The method is suitable for the synthesis of both electron rich and electron deficient compounds, and it shows high tolerance toward different functional groups (halides, ester, nitro, cyano groups). Thus, a sustainable photocatalytic alternative to the Meerwein chlorosulfonylation reaction is offered.