FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)(=O)=O.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[K+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:21][C:22]1[CH:27]=[C:26]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[O:10][C:9](=[O:18])[CH:8]=2)[CH:25]=[CH:24][CH:23]=1
To a solution of 7-methyl-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate (5 g, 16.2 mmol) and 3-fluorobenzeneboronic acid (2.5 g, 17.9 mmol) in THF (75 mL), tricyclohexylphosphine (227 mg, 0.81 mmol) and potassium fluoride (3.3 g, 56.8 mmol) were added. The reaction mixture was purged twice with nitrogen before palladium (II) acetate (146 mg, 0.65 mmol) was added. After 16 hours stirring at room temperature, the reaction mixture was filtered over celite and the filtrate was concentrated under reduced pressure. The crude residue obtained was purified by column chromatography (CH2Cl2/Hexanes, 70:30). To afford the title compound 1H NMR (400 MHz, acetone-d6): 7.7-7.6 (m, 1H), 7.45-7.3 (m, 4H), 7.26 (s, 1H), 7.18 (d, 1H), 6.3 (s, 1H), 2.47 (s, 3H).
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