反应详情

Tricyclic bromide 11 (0.2 g, 0.75 mmol) in toluene (20 mL) and EtOH (10 mL) was treated with solid Na2CO3 (0.199 g, 1.88 mmol), LiCl (0.095 g, 2.25 mmol), phenylboronic acid (0.138 g, 1.13 mmol), and water (0.50 mL). The solution was degassed and tetrakis(triphenylphosphine)palladium(0) (43 mg, 5 mol %) was added. The solution was heated at reflux for 5 h, and then cooled to ambient temperature and diluted with water (20 mL). The aqueous layer was adjusted to pH=7-8 with saturated aqueous K2CO3 and extracted with EtOAc (20 mL×3). The organic solution was washed with water and brine, and dried (Na2SO4), filtered, and concentrated. The crude product was recrystallized (CH2Cl2/MeOH/hexanes) to yield the 2-phenyltricycle as a pale-yellow solid, 183 mg (93%). mp 249-255° C. (dec); 1H NMR (CDCl3/CD4OD) δ 3.14 (m, 2H), 3.53 (m, 2H), 7.23 (t, 1H, J=7.7 Hz), 7.33 (m, 1H), 7.44 (m, 2H), 7.55 (m, 3H), 7.83 (d, 1H, J=7.7 Hz); HRMS (M+H) Calcd for C17H14N2O+H, 263.1184, Found: 263.1189; Anal. (C17H14N2O.0.8 H2O) C, H, N.

1. customThe solution was degassed
2. additiontetrakis(triphenylphosphine)palladium(0) (43 mg, 5 mol %) was added
3. temperatureThe solution was heated
4. temperatureat reflux for 5 h
5. additiondiluted with water (20 mL)
6. extractionextracted with EtOAc (20 mL×3)
7. washThe organic solution was washed with water and brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was recrystallized (CH2Cl2/MeOH/hexanes)
12. customto yield the 2-phenyltricycle as a pale-yellow solid, 183 mg (93%)