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Borates M[C 6 F 5 BF 3 ] (M = K, Li, Bu 4 N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC 6 F 4 BF 3 ] and M[2-RC 6 F 4 BF 3 ]. When R is Me or Bu, the nucleophilic substitution of the fluorine atom at the para position to boron is the predominant route. When R = Ph, the ratio M[4-RC 6 F 4 BF 3 ]/M[2-RC 6 F 4 BF 3 ] is ca. 1:1. Substitution of the fluorine atom at the ortho position to boron is solely caused by the coordination of RLi via the lithium atom with the fluorine atoms of the BF 3 group. This differs from the previously reported substitution in K[C 6 F 5 BF 3 ] by O- and N-nucleophiles that did not produce K[2-NuC 6 F 4 BF 3 ].

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles

Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles