Scheme 7. Scope of the Ru-Catalyzed Arylation of (Hetero)Aromatics 1c–z, 4–7 with Bromoarenes 2a–b.

Standard conditions: bromoarene 2 (0.5 mmol), (fluoro)arene 1 (3 equiv), (NMe₄)(4-FC₆H₄CO₂) (0.35 equiv), (NMe₄)OPiv (0.4 equiv), (NMe₄)(OC(CF₃)₃) (2.5 equiv), C5 (4 mol %), and t-BuCN (3 equiv) stirred at 115 °C under N₂ in a closed vessel for 16 h. Yields are of pure, isolated products.

t-BuCN (6 equiv).

Reaction time was 2 h.

1 (10 equiv).

1 (5 equiv).

See Figures 7 and S8 and Table S12.

Detected in traces by ¹⁹F NMR.

Yields in brackets are from reactions carried out without (NMe₄)(4-FC₆H₄CO₂).

(Hetero)arene (0.5 mmol) and bromoarene 2 (1 equiv).

Yield determined by ¹H NMR analysis.