Transition‐Metal‐Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles

Abstract

A chemoselective C(sp² )-C(sp² ) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (S_N Ar). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.