Onium Transfer Reaction of (β,β-Dialkylvinyl)(phenyl)iodonium Tetrafluoroborates via an Alkylidene Carbene Pathway: Synthesis of Group 15 Alkenyl(triphenyl)- and Group 16 Alkenyl(diphenyl)onium Salts

Group 15 1-alkenyl(triphenyl)onium (P, As, Sb) tetrafluoroborates were prepared via an onium transfer reaction of alkenyl(phenyl)iodonium tetrafluoroborates under mild conditions. The reaction involves base-induced reductive α-elimination of the iodonium salts, followed by nucleophilic trapping of the resulting free alkylidene carbenes with group 15 element-centered nucleophiles. The onium transfer reaction of the alkenyliodonium salts also produced group 16 1-alkenyl(diphenyl)onium (S, Se, Te) tetrafluoroborates in good yields.