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Literature DB >> 27239806

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

Jiangtao Zhu¹, Manuel Pérez¹, Douglas W Stephan².

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.

Entities: Chemical

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

Year: 2016 PMID： 27239806 DOI： 10.1002/anie.201603627

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

6 in total

1. Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

Authors: Aristidis Vasilopoulos; Dung L Golden; Joshua A Buss; Shannon S Stahl
Journal: Org Lett Date: 2020-07-29 Impact factor: 6.005

2. Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Authors: Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal: Org Lett Date: 2018-05-10 Impact factor: 6.005

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

1. Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

2. Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

3. Silylated cyclopentadienes as competent silicon Lewis acid catalysts.

4. Phosphonic acid mediated practical dehalogenation and benzylation with benzyl halides.

5. Aluminum-catalyzed tunable halodefluorination of trifluoromethyl- and difluoroalkyl-substituted olefins.

6. Tetragonal phosphorus(v) cations as tunable and robust catalytic Lewis acids.