[C:1]1(Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(N(C)C2C=CC=CC=2)C=1P(C1CCCCC1)C1CCCCC1>[C:1]1([CH:16]([CH3:17])[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][CH:11]=2)=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are phenyl chloride (111.0 mg, 0.99 mmol), 1-(4-methylphenyl)-1-propanone (177.8 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (115.8 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 16.5 h. 2-Phenyl-1-(p-tolyl)-1-propanone (216.5 mg, contaminated with 11.9% of 1-(4-methylphenyl)propanone determined by 1H NMR) was obtained with a yield of 90% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.87-7.80 (m, 2H, ArH), 7.30-7.20 (m, 4H, ArH), 7.20-7.08 (m, 3H, ArH), 4.64 (q, J=7.0 Hz, 1H, CH), 2.27 (s, 3H, ArCH3), 1.50 (d, J=7.0 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 199.7, 143.3, 141.6, 133.7, 129.0, 128.74, 128.72, 127.5, 126.6, 47.5, 21.3, 19.3; IR (neat) v (cm−1) 3061, 3028, 2975, 2930, 2870, 1682, 1606, 1570, 1492, 1452, 1408, 1372, 1332, 1304, 1253, 1225, 1210, 1177, 1008; MS (70 eV, EI) m/z (%): 224 (M+, 0.64), 119 (100).
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