Borate-mediated aryl polyfluoroalkoxylation under transition-metal-free conditions

We describe the transition-metal-free coupling for polyfluoroalkoxy arenes using polyfluoroalkoxy borates, which serve as counterions to diaryliodonium salts and transferring mediators of polyfluoroalkoxy groups. This strategy demonstrates high functional group compatibility owing to the low nucleop...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-09, Vol.6 (76), p.1552-1555
Main Authors: Kikushima, Kotaro, Tsuda, Tomoka, Miyamoto, Naoki, Kita, Yasuyuki, Dohi, Toshifumi
Format: Article
Language:English
Subjects:
Aromatic compounds
Borates
Functional groups
Transition metals
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Summary:We describe the transition-metal-free coupling for polyfluoroalkoxy arenes using polyfluoroalkoxy borates, which serve as counterions to diaryliodonium salts and transferring mediators of polyfluoroalkoxy groups. This strategy demonstrates high functional group compatibility owing to the low nucleophilicity of the borate mediator, thus offering a practical approach for synthesizing diverse polyfluoroalkoxy arenes. We report boron-intermediary ligand transfer of diaryliodonium salt, synthesizing polyfluorolalkyl aryl ethers in the absence of transition metal catalyst or base.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc04008b