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. 2016 Jul 11;55(29):8448-51.
doi: 10.1002/anie.201603627. Epub 2016 May 30.

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

Jiangtao Zhu  1 , Manuel Pérez  1 , Douglas W Stephan  2
Affiliations

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

Jiangtao Zhu et al. Angew Chem Int Ed Engl. .

Abstract

The activation and cleavage of benzyl fluorides by the electrophilic organofluorophosphonium catalyst, [(C6 F5 )3 PF][B(C6 F5 )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.

Keywords: C(sp3)-C(sp3) coupling; arylation reactions; benzyl fluorides; homogeneous catalysis; phosphonium cations.

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