C−C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation

C−C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation

The activation and cleavage of benzyl fluorides by the electrophilic organofluorophosphonium catalyst, [(C6F5)3PF][B(C6F5)4], is reported and used for the preparation of 1,1‐diarylalkanes (37 examples) and substituted aryl homoallylic alkenes (14 examples). This procedure involves mild conditions, a...

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Veröffentlicht in:Angewandte Chemie International Edition 2016-07, Vol.55 (29), p.8448-8451
Hauptverfasser: Zhu, Jiangtao, Pérez, Manuel, Stephan, Douglas W.
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes
Aromatic compounds
arylation reactions
benzyl fluorides
C(sp3)-C(sp3) coupling
Catalysts
Fluorides
homogeneous catalysis
phosphonium cations
Silanes
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Zusammenfassung:The activation and cleavage of benzyl fluorides by the electrophilic organofluorophosphonium catalyst, [(C6F5)3PF][B(C6F5)4], is reported and used for the preparation of 1,1‐diarylalkanes (37 examples) and substituted aryl homoallylic alkenes (14 examples). This procedure involves mild conditions, avoids harmful waste, and is compatible with a range of substituted arenes and allylic silanes. C‐F functionalization: Benzyl fluorides are activated by [(C6F5)3PF][B(C6F5)4], affording catalytic routes to 37 1,1‐diarylalkanes and 14 substituted aryl homoallylic alkenes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201603627