574-39-0

Vinyl acetate (1a, 167 mg, 1 mmol) and carbazole (2, 430 mg, 5 mmol) were mixed with [Ir(Cl)(cod)]2 (6.7 mg, 0.01 mmol), Na2CO3 (127 mg, 1.2 mmol) and toluene (1 mL) under argon protection and the reaction was stirred for 15 h at 100 °C. The reaction was carried out by GC analysis. The conversion and yield of the product were calculated by gas chromatography (GC) analysis with internal standard method, and the yield of 1-(9H-carbazol-9-yl)ethanone (3a) was obtained as 96%. Product 3a was purified by column chromatography (using 230-400 mesh silica gel with hexane containing 5% Et3N as eluent) in a final yield of 94% (181 mg). For product 3e, the separation was carried out by column chromatography only (using 70-230 mesh alumina and hexane as eluent).

[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 11, p. 1192 - 1197
[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, # 11, p. 1504 - 1509
[3] Synlett, 2017, vol. 28, # 6, p. 719 - 723