1,10-Phenanthroline → 1-Oxo-2,6-diphenyl-1lambda~5~-pyridine

Participants

Reaction Steps

Copper(I) iodide (19 mg, 0.1 mmol), iodobenzene (408 mg, 2.0 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol), pyridine N-oxide (95 mg, 1.0 mmol), t-BuOLi (145 mg, 1.8 mmol), and anhydrous DMPU (0.5 mL), 125° C., 1 hour. After column chromatography (ethyl acetate, then 15% MeOH in ethyl acetate) 50 mg of 2,6-diphenylpyridine 1-oxide (20%) was obtained as an off-white solid. Additionally, 2-phenylpyridine 1-oxide (100 mg, 58%) was obtained as a colorless solid. These compounds are known.7,12 2-Phenylpyridine 1-oxide: Rf=0.46 (3/7 methanol/ethyl acetate). The molecule structure of 2-phenylpyridine 1-oxide and its 1H NMR spectrum are shown in FIG. 59. 1H NMR (300 MHz, CDCl3) δ 7.17-7.34 (m, 2H), 7.38-7.53 (m, 4H), 7.80 (dd, J=7.7 Hz, 1.7 Hz, 2H), 8.33 (d, J=6.0 Hz, 1H). 2,6-Diphenylpyridine 1-oxide: Rf=0.30 (1/1 ethyl acetate/hexanes). 1H NMR (300 MHz, CDCl3) δ 7.28-7.52 (m, 9H), 7.80-7.87 (m, 4H).

Provenance & Evidence