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Representative Procedure: Synthesis of 2,3-Diphenyl-indole (4b)
2-Chloroaniline (1a; 133 mg, 1.04 mmol), and tolan (2b; 267 mg, 1.50 mmol) were added to a solution of Ru3(CO)12 (6.4 mg, 0.01 mmol, 1 mol%) and NH4PF6 (4.9 mg, 0.03 mmol, 3 mol%) in toluene (1 mL) and the resulting mixture was stirred
for 18 h at 105 °C. Thereafter, t-BuOK (224 mg, 2.00 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol, 5 mol%), 5 (21.3 mg, 0.05 mmol, 5 mol%), and toluene (2 mL) were added and the mixture was stirred
at 105 °C for 24 h. Et2O (50 mL) and brine (50 mL) were added to the cold suspension. The separated aqueous
phase was washed with Et2O (2 × 50 mL). Drying with MgSO4 and purification by column chromatog-raphy (silica gel; n-pentane-Et2O, 10:1 to 6:1) yielded 2,3-diphenylindole (4b; 248 mg, 89%) as a yellow solid; mp 129.8-130.0 °C. 1H NMR (400 MHz): δ = 8.23 (s, 1 H), 7.71 (d, J = 8.6 Hz, 1 H), 7.49-7.14 (m, 13 H).
13C NMR (100 MHz): δ = 135.8, 135.0, 134.0, 132.7, 130.1, 128.7, 128.6, 128.5, 128.1,
127.7, 126.2, 122.7, 120.4, 119.7, 115.0, 110.8. IR (ATR): 3396, 3052, 1600, 1533,
1455, 1439, 1371, 1328, 1249, 1152, 1070, 1011, 965, 919, 828, 763, 740, 693 cm-1. HRMS (EI): m/z calcd for C20H15N: 269.1204; found: 269.1202.