Scheme 3.

Scope II: Coupling of various silylated aryldiazenes with functionalized polyfluorarenes. All reactions were performed on a 0.30 mmol scale at room temperature. Regioisomeric ratios (para : ortho : meta or β : α) were determined by quantitative ¹⁹F NMR analysis with hexafluorobenzene as an internal standard. Yields are isolated yields of para (β for 3 hf) regioisomers after purification. [a] 10 equiv of the polyfluorarene used. [b] The reaction time was 12 h. [c] Yield of isolated product on a 1.30 mmol scale after flash chromatography on silica gel in parentheses. [d] Yield determined by quantitative ¹⁹F NMR analysis with hexafluorobenzene as an internal standard. n.d.=not determined.