Plumbyl anions reaction with

Lead(IV) trifluoroacetate in TFAH is a very reactive electrophile that is capable of plumbylating less electron-rich arenes. Nonetheless, the use of trifluoroacetate anions in the plumbylation reactions should be avoided, because aryllead(IV) tri-fluoroacetates are unstable compounds that readily decompose to the corresponding aryl trifluoroacetates and biaryls [34—37, 40, 41]. It has been reported [41] that 4-FC6H4ArPb(TFA)3 is reasonably stable and can be isolated from the reaction of Pb(TFA)4/TFAH with fluorobenzene. A mechanistic study [41] indicated an electrophilic substitution path for the plumbylation reaction, which seemed to be substantially more para-selective than mercuration and thallation. For example, the plumbylation of toluene with Pb(OAc)4 in dichloroacetic acid has been reported [41] to occur with >90 % para-selectivity. 

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