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Arisawa M, Tanii S, Tazawa T, et al. Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides. Chem Commun (Camb). 2016;52(76):11390-11393doi: 10.1039/c6cc05400e.
Arisawa, M., Tanii, S., Tazawa, T., & Yamaguchi, M. (2016). Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides. Chemical communications (Cambridge, England), 52(76), 11390-11393. https://doi.org/10.1039/c6cc05400e
Arisawa, Mieko, et al. "Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides." Chemical communications (Cambridge, England) vol. 52,76 (2016): 11390-11393. doi: https://doi.org/10.1039/c6cc05400e
Arisawa M, Tanii S, Tazawa T, Yamaguchi M. Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides. Chem Commun (Camb). 2016 Sep 15;52(76):11390-11393. doi: 10.1039/c6cc05400e. PMID: 27709178.
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Chem Commun (Camb). 2016 Sep 15;52(76):11390-11393. doi: 10.1039/c6cc05400e.

Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides.

Chemical communications (Cambridge, England)

Mieko Arisawa, Saori Tanii, Takeru Tazawa, Masahiko Yamaguchi

Affiliations

  1. Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. [email protected] [email protected].

PMID: 27709178 DOI: 10.1039/c6cc05400e

Abstract

A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.

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