[OH:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.O>C([O-])([O-])=O.[K+].[K+].CC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([OH:1])[CH:7]=2)=[CH:13][CH:14]=1To a solution of 3-hydroxyphenylboronic acid (1.00 g, 7.3 mmol) in 2M aqueous K2CO3 (4 mL) was added a solution of 4-iodoanisole (1.70 g, 7.3 mmol) in acetone (4 mL). A homogeneous mixture was obtained by sequential addition of water (60 mL) and acetone (30 mL). Catalytic Pd(OAc)2 was added (160 mg, 0.73 mmol) and the mixture was stirred for 10 min at room temperature. The acetone was removed from the dark brown solution in vacuo and the resultant aqueous mixture was acidified with 1N HCl (20 mL) and extracted with ethyl acetate (75 mL). The organic layer was washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was suspended in dichloromethane and adsorbed onto silica gel and purified by flash chromatography using hexanes-ethyl acetate (3:1) to yield 1.20 g (82%) 56 as a white solid after solvent removal.
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