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15. General procedure for the Pd(OAc)2-catalyzed reaction of alkenyl tosylates with
organoindium reagents: organoindium reagent 2 (0.5 mmol) in THF (1.0 mL)
was added to
a mixture of Pd(OAc)2 (1 mol %) and alkenyl tosylate 1
(0.5 mmol) in THF (2.0 mL) at room temperature. After completion of the
reaction as indicated by TLC (less than 1 min), the solvent was evaporated. The
residue was then diluted with EtOAc (10 mL), washed with H2O (10 mL), dried
by anhydrous MgSO4. Evaporation of the solvent followed by purification on
silica gel provided the corresponding product 3. Data of selected example:
4-(4-methoxyphenyl)coumarin (3a)4f, Yield: 98%; 1H NMR (400 MHz, CDCl3):
3.89 (s, 3H), 6.35 (s, 1H), 7.05 (d, J = 8.7 Hz, 2H), 7.22–7.26 (m, 1H), 7.40–7.42
(m, 3H), 7.54–7.57 (m, 2H). m/z (ESI): 253 (M++H) (for details, please see
Supplementary data).