Tris(1,1-dimethylethyl)phosphine → 11-(4-Carbazolylphenyl)indolo[2,3-a]carbazole

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Reaction Conditions

Reaction Steps

In a 100-ml three-necked flask were placed 0.21 g (0.94 mmole) of palladium(II) acetate, 20 ml of xylene, and 0.76 g (3.76 mmoles) of tri-tert-butylphosphine and the mixture was heated at 60° C. with stirring for 30 minutes. The resulting solution was sent into a solution that had been prepared by dissolving 4.61 g (0.0180 mole) of indolo[2,3-a]carbazole, 5.8 g (0.018 mole) of 4-carbazolylbromobenzene, and 7.7 g (0.080 mole) of sodium tert-butoxide in 180 ml of xylene and heated at 60° C. in a stream of nitrogen and the combined solution was heated up to 130° C. and kept at this temperature for 5 hours with stirring. The solution was cooled to room temperature, 200 ml of water was added, and the organic layer was separated and concentrated under reduced pressure to give a crude product. The crude product was purified by crystallization from dichloromethane and ethanol, the solvent was distilled off under reduced pressure, and 4.2 g (0.0084 mole, 47% yield) of 11-(4-carbazolylphenyl)indolo[2,3-a]carbazole was obtained.

Provenance & Evidence