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Issue 3, 2015
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Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines

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Abstract

Stepwise oxidation of 1,8-bis(diphenylphosphino)naphthalene and a series of (oligo)methylene-linked diphosphines with XeF2 followed by fluoride abstraction yields a family of compounds featuring phosphine, phosphonium and phosphorane moieties in close proximity. The bisphosphonium ions [(C10H6)(Ph2PF)2]2+ (5) and [CH2(Ph2PF)2]2+ (9a) exhibit remarkable Lewis acidity arising from the proximity of the phosphonium centers. The effectiveness of bisphosphonium dications (5, 9a–e) is examined in a series of Lewis acid catalysed transformations.

Graphical abstract: Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines

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Publication details

The article was received on 06 Jan 2015, accepted on 27 Jan 2015 and first published on 27 Jan 2015


Article type: Edge Article
DOI: 10.1039/C5SC00051C
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Citation: Chem. Sci., 2015,6, 2016-2021
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    Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines

    M. H. Holthausen, R. R. Hiranandani and D. W. Stephan, Chem. Sci., 2015, 6, 2016
    DOI: 10.1039/C5SC00051C

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