Cu(OTf)2‑Mediated Fluorination of Aryltrifluoroborates with Potassium Fluoride

Cu(OTf)2‑Mediated Fluorination of Aryltrifluoroborates with Potassium Fluoride

This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 °C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1...

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Veröffentlicht in:Journal of the American Chemical Society 2013-11, Vol.135 (44), p.16292-16295
Hauptverfasser: Ye, Yingda, Schimler, Sydonie D, Hanley, Patrick S, Sanford, Melanie S
Format: Artikel
Sprache:eng
Schlagworte:
Boranes - chemistry
Fluorides - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Mesylates - chemistry
Molecular Structure
Potassium Compounds - chemistry
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Zusammenfassung:This Communication describes the Cu(OTf)2-mediated fluorination of aryltrifluoroborates with KF. The reaction proceeds under mild conditions (at 60 °C over 20 h) and shows a broad substrate scope and functional group tolerance. The Cu is proposed to play two separate roles in this transformation: (1) as a mediator for the aryl–F coupling and (2) as an oxidant for accessing a proposed CuIII(aryl)(F) intermediate.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja408607r