Phosphines and phosphonates having alkenyl groups are shown to form reactive electrophiles in superacid-catalyzed reactions. The electrophiles react with benzene and substituted arenes in Friedel-Crafts reactions (eq 1). Mechanisms are proposed involving superelectrophilic phosphonium-carbenium and oxophosphonium-carbenium dications. It is also shown that this chemistry is effective in preparing phosphine and phosphonate-functionalized polystyrene resins (eq 2).

Phosphonium-carbenium and oxophosphonium-carbenium dications in Friedel-Crafts reactions

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ACS Fall 2022

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