Electrophilic phenoxy-substituted phosphonium cations

Abstract

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.