Isolable fluorinated triphenylmethyl cation salts of [HCB₁₁Cl₁₁]^-: demonstration of remarkable hydride affinity.

ABSTRACT: Significantly fluorinated triarylmethyl cations have long attracted attention as potentially accessible highly reactive carbocations, but their isolation in a convenient form has proved elusive. We show that abstraction of chloride with a cationic silylium reagent leads to the facile formation of di-, tetra-, and hexafluorinated trityl cations, which could be isolated as analytically pure salts with the [HCB₁₁Cl₁₁]^- counterion and are compatible with (halo)arene solvents. The F₆Tr⁺ cation carrying six meta-F substituents was computationally predicted to possess up to 20% higher hydride affinity than the parent triphenylmethyl cation Tr⁺. We report that indeed F₆Tr⁺ displays reactivity unmatched b

SUBMITTER: Gunther SO 

PROVIDER: S-EPMC9067617 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature