Palladium 10% on Carbon (wetted with ca. 55% Water) [Useful catalyst for coupling reaction, etc.]

• 4-Chlorobenzotrifluoride [C0305]
• Phenylboronic Acid (contains varying amounts of Anhydride) [B0857]
• Palladium 10% on Carbon (wetted with ca. 55% Water) [Useful catalyst for coupling reaction, etc.] [P1785]
• K₂CO₃ [P1748]
• N,N-Dimethylacetamide (= DMA)

4-Chlorobenzotrifluoride (500 mg, 2.77 mmol), phenylboronic acid (506 mg, 4.15 mmol), palladium on carbon (14.7 mg) and potassium carbonate (765 mg, 5.54 mmol) were dissolved in DMA/H₂O (4.5 mL/0.5 mL) and stirred at 80 °C for 24 hours. The reaction mixture was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 0:100 - 5:95) to give 4-(trifluoromethyl)-1,1'-biphenyl as a white solid (485 mg, 79% yield).

The reaction mixture was monitored by UPLC.

4-(Trifluoromethyl)-1,1'-biphenyl

¹H NMR (270 MHz, CDCl₃); δ 7.60-7.54 (m, 4H), 7.49-7.46 (m, 3H), 7.41-7.36 (m, 2H).

• Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium
  • C. R. LeBlond, A. T. Andrews, Y. Sun, J. R. Sowa, Org. Lett. 2001, 3, 1555.