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General Procedure for the Synthesis of 7: To an oven-dried Schlenk flask (25 mL) was charged 4-coumarin compound 3 (0.5 mmol), NiCl2
(PPh3)2 (0.2 equiv), PPh3 (0.4 equiv), zinc dust (2.2 mmol) and dry toluene (3 mL) under argon. The resulting mixture was heated to 90 °C. The aryl halide 5 (0.6 mmol) was then added dropwise through micro-syringe pump over 3 h. After the addition, the reaction mixture was stirred at the same temperature until completion. The reaction mixture was cooled down to r.t., quenched with 5% HCl and diluted by CH2Cl2. The mixture was stirred vigorously at r.t. until the solution was clear. The organic layer was separated and the water layer was extracted with CH2Cl2 (3 × 10 mL). The combined organic layer was washed with sat. aq NaHCO3, brine, and dried over Na2SO4. The solution was concentrated under vacuum; the obtained residue was purified by silica column chromato-graphy to give the corresponding cross-coupling product 7 (selected characterization data of 7 are listed as follows).
15 Compound 7c. 1H NMR (300 MHz, CDCl3): d = 9.69 (s, 1 H), 7.86 (m, 1 H), 7.54 (m, 1 H), 7.45 (m, 1 H), 7.22-7.16 (m, 2 H), 7.01 (m, 1 H), 6.40 (s, 1 H), 4.05 (s, 3 H), 3.70 (s, 3 H). MS (EI): m/z (%) = 310 (71) [M+], 295 (100). IR (KBr): 3088, 2947, 2837, 2733, 1729, 1695, 1683, 1604, 1584, 1566 cm-1. Anal. Calcd for C18H14O5: C, 69.67; H, 4.55. Found: C, 69.86; H, 4.57.
16 Compound 7f. 1H NMR (300 MHz, CDCl3): d = 8.08 (d, J = 2.1 Hz, 1 H), 7.64 (s, 1 H), 7.54 (d, J = 7.5 Hz, 1 H), 7.51 (d, J = 7.5 Hz, 1 H), 7.42-7.21 (m, 4 H), 6.45 (d, J = 2.1 Hz, 1 H), 3.93 (s, 3 H). 13C NMR (75.5 MHz, CDCl3): d = 175.12, 160.67, 157.84, 154.08, 153.90, 151.45, 148.05, 132.41, 127.02, 124.91, 124.52, 120.90, 120.03, 118.95, 117.70, 117.45, 105.45, 56.28. MS (EI): m/z (%) = 320 (4) [M+], 292 (10.00). IR (KBr): 3078, 2963, 1720, 1649, 1610, 1488, 1446, 1334, 1271 cm-1. HRMS: m/z calcd for C19H12O5: 320.0685; found: 320.0734.
17 Compound 7h. 1H NMR (300 MHz, CDCl3): δ = 8.05 (s, 1 H), 7.65 (s, 1 H), 7.55-7.30 (m, 4 H), 7.11 (s, 1 H), 6.42 (s, 1 H), 3.94 (s, 3 H), 2.34 (s, 3 H). 13C NMR (75.5 MHz, CDCl3): δ = 174.84, 160.58, 157.73, 153.66, 151.79, 151.20, 147.65, 133.95, 133.21, 126.31, 124.64, 120.69, 119.76, 118.46, 117.47, 116.90, 105.26, 59.01, 20.91. MS (EI):
m/z (%) = 335 (18) [M+ + 1], 334 (78) [M+], 333 (21) [M+ - 1], 306 (100). IR (KBr): 3078, 2959, 2929, 2498, 1719, 1698, 1646, 1618, 1568, 1488, 821 cm-1. HRMS: m/z calcd for C20H14O5: 334.0841; found: 334.0874.
18 Compound 7j. 1H NMR (300 MHz, CDCl3): δ = 9.70 (s, 1 H), 7.54-7.30 (m, 5 H), 6.80 (s, 1 H), 6.39 (d, J = 15 Hz, 2 H). MS (EI): m/z (%) = 312 (71) [M+], 269 (100). IR (KBr): 3075, 2913, 2861, 1725, 1682, 1610, 1571, 1504, 1482, 1440, 1369, 1268, 1253 cm-1. HRMS: m/z calcd for C17H9FO5: 312.0434; found: 312.0385.
19 Compound 7m. 1H NMR (300 MHz, CDCl3): δ = 10.16 (s, 1 H), 8.09 (d, J = 9.0 Hz, 2 H), 7.89 (d, J = 9.0 Hz, 2 H), 7.74-7.58 (m, 4 H), 7.37 (d, J = 9.3 Hz, 1 H), 7.16 (d, J = 8.7 Hz, 1 H), 6.51 (s, CH, 1 H). MS (EI): m/z (%) = 301 (20) [M+ + 1], 300 (91) [M+], 272 (100). IR (KBr): 1733, 1631, 1601, 1549, 1500, 1470, 1375, 1209 cm-1. HRMS: m/z calcd for C20H12O3: 300.0786; found: 300.0809.
