Reaction Steps
Pd(PPh3)4 (7.43 mg, 6.43 μmol) was added to a solution of the triflate 44 (236 mg, 0.16 mmol), 4-methoxyphenylboronic acid (63 mg, 0.42 mmol), TEA (0.13 mL, 98 mg, 0.97 mmol) in H2O (0.8 mL), EtOH (5 mL) and toluene (5 mL) at room temperature. The reaction mixture was heated in the microwave at 100° C. for 30 minutes after which time TLC (80:20 v/v EtOAc/hexane) revealed the complete consumption of the starting material. Excess solvent was removed by evaporation in vacuo and the resulting residue was dissolved in EtOAc (50 mL), washed with H2O (20 mL), brine (20 mL) and dried (MgSO4). Filtration and evaporation of solvent afforded the crude product which was purified by flash column chromatography (gradient elution: 80:20 v/v Hexane/EtOAc to 50:50 v/v Hexane/EtOAc) to afford C2-aryl product 45 as a yellow glass (117 mg, 52%): 1H NMR (400 MHz, CDCl3) δ 7.35 (s, 2H), 7.31 (s, 2H), 7.31-7.27 (m, 6H), 6.90 (d, 4H, J=8.8 Hz), 6.76 (s, 2H), 5.92 (d, 2H, J=8.8 Hz), 5.23 (d, 2H, J=12.0 Hz), 4.20 (d, 2H, J=12.1 Hz), 4.14-4.05 (m, 4H), 4.04-3.95 (m, 2H), 3.93 (s, 6H), 3.83 (s, 6H), 3.34 (ddd, 2H, J=16.3, 10.4, 2.0 Hz), 2.86-2.75 (m, 2H), 2.02-1.94 (m, 4H), 1.72-1.66 (m, 2H), 0.93 and 0.86 (s×2, 18H), 0.28 and 0.25 (s×2, 12H); 13C NMR (100 MHz, CDCl3) δ 163.7, 159.1, 153.7, 150.8, 149.3, 127.8, 126.3, 126.1, 125.4, 122.3, 122.2, 114.3, 114.2, 110.9, 95.3, 87.3, 74.8, 68.8, 61.5, 56.2, 55.4, 35.3, 28.8, 25.7, 22.8, 17.9, −4.0 and −5.1.
