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Yang L, Zhang CP. Revisiting the Balz-Schiemann Reaction of Aryldiazonium Tetrafluoroborate in Different Solvents under Catalyst- and Additive-Free Conditions. ACS Omega. 2021;6(33):21595-21603doi: 10.1021/acsomega.1c02825.
Yang, L., & Zhang, C. P. (2021). Revisiting the Balz-Schiemann Reaction of Aryldiazonium Tetrafluoroborate in Different Solvents under Catalyst- and Additive-Free Conditions. ACS omega, 6(33), 21595-21603. https://doi.org/10.1021/acsomega.1c02825
Yang, Lian, and Zhang, Cheng-Pan. "Revisiting the Balz-Schiemann Reaction of Aryldiazonium Tetrafluoroborate in Different Solvents under Catalyst- and Additive-Free Conditions." ACS omega vol. 6,33 (2021): 21595-21603. doi: https://doi.org/10.1021/acsomega.1c02825
Yang L, Zhang CP. Revisiting the Balz-Schiemann Reaction of Aryldiazonium Tetrafluoroborate in Different Solvents under Catalyst- and Additive-Free Conditions. ACS Omega. 2021 Aug 13;6(33):21595-21603. doi: 10.1021/acsomega.1c02825. eCollection 2021 Aug 24. PMID: 34471763; PMCID: PMC8388107.
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ACS Omega. 2021 Aug 13;6(33):21595-21603. doi: 10.1021/acsomega.1c02825. eCollection 2021 Aug 24.

Revisiting the Balz-Schiemann Reaction of Aryldiazonium Tetrafluoroborate in Different Solvents under Catalyst- and Additive-Free Conditions.

ACS omega

Lian Yang, Cheng-Pan Zhang

Affiliations

  1. School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China.

PMID: 34471763 PMCID: PMC8388107 DOI: 10.1021/acsomega.1c02825

Abstract

The thermal and photochemical Balz-Schiemann reaction in commonly used solvents was revisited under catalyst- and additive-free conditions. The study showed that using low- or non-polar solvents could improve the pyrolysis and photolysis of aryldiazonium tetrafluoroborates, enabling effective fluorination at a low temperature or under visible-light irradiation. PhCl and hexane were exemplified as cheap and reliable solvents for both reactions, providing good to excellent yields of aryl fluorides from the corresponding diazonium tetrafluoroborates. The combination of slight heating with visible-light irradiation was beneficial for the transformation of stable aryldiazonium tetrafluoroborates. Nevertheless, the electronic and steric nature of aryldiazonium tetrafluoroborates still had a pivotal effect on both fluorinations even in these solvents.

© 2021 The Authors. Published by American Chemical Society.

Conflict of interest statement

The authors declare no competing financial interest.

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