4.7 Article

Electrophilic phenoxy-substituted phosphonium cations

Journal

DALTON TRANSACTIONS
Volume 45, Issue 45, Pages 18156-18162

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6dt03544b

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Funding

  1. NSERC of Canada
  2. Canada Research Chair
  3. NSERC of Canada Postdoctoral fellowship

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A family of electrophilic phenoxy-substituted phosphonium salts [(RO) P(C6F5)(3)][B(C6F5)(4)] (R = C6H5, 4-FC6H4, 2,4-F2C6H3, C6F5) have been synthesized and their air stability was evaluated. Computations of the fluoride ion affinity and global electrophilicity index have been used to compare the electrophilicity of these phosphonium salts. The Lewis acidity of these phosphonium salts was probed computationally and experimentally in a Friedel-Crafts-type dimerization, hydrodefluorination, hydrosilylation, hydrodeoxygenation, and dehydrocoupling reactions.

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