P-Chloroacetophenone → 4-Acetylbiphenyl

Participants

Reaction Steps

According to General Procedure A, a mixture of 4-chloroacetophenone (65 μL, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and ligand 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. After evaporation of the solvent, recrystallization from hexane containing a small amount of EtOAc gave 51b (86 mg, 88%) as colorless crystals. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, 2H, J=8.4 Hz), 7.69 (d, 2H, J=8.4 Hz), 7.63 (d, 2H, J=7.2 Hz), 7.50-7.40 (m, 3H), 2.64 (s, 3H); 13C NMR (75.5 MHz, CDCl3) δ 197.7, 145.8, 139.8, 135.8, 128.93, 128.89, 128.2, 127.24, 127.20, 26.6.

Provenance & Evidence