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Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines.


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.

SUBMITTER: Holthausen MH 

PROVIDER: S-EPMC5496503 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Electrophilic bis-fluorophosphonium dications: Lewis acid catalysts from diphosphines.

Holthausen Michael H MH   Hiranandani Rashi R RR   Stephan Douglas W DW  

Chemical science 20150127 3


Stepwise oxidation of 1,8-bis(diphenylphosphino)naphthalene and a series of (oligo)methylene-linked diphosphines with XeF<sub>2</sub> followed by fluoride abstraction yields a family of compounds featuring phosphine, phosphonium and phosphorane moieties in close proximity. The bisphosphonium ions [(C<sub>10</sub>H<sub>6</sub>)(Ph<sub>2</sub>PF)<sub>2</sub>]<sup>2+</sup> (<b>5</b>) and [CH<sub>2</sub>(Ph<sub>2</sub>PF)<sub>2</sub>]<sup>2+</sup> (<b>9a</b>) exhibit remarkable Lewis acidity arising  ...[more]

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