Tris(1,1-dimethylethyl)phosphine → 9-[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-10-phenylanthracene

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Reaction Steps

Into a 100 mL three-neck flask were added 501 mg (1.5 mmol) of 9-bromo-10-phenylanthracene, 504 mg (1.5 mmol) of N,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA), and 500 mg (5.2 mmol) of sodium-tert-butoxide, and the atmosphere in the flask was substituted by nitrogen. Thereafter, 10 mL of toluene and 0.1 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to the mixture. This mixture was stirred under reduced atmosphere to be degassed. After degassing, 43 mg (0.075 mmol) of bis(dibenzylideneacetone)palladium(0) was added. This mixture was stirred at 80° C. for 3 hours under nitrogen. After the reaction, the mixture was added with about 20 mL of toluene and then washed with water. An aqueous layer was extracted with toluene, and the extracted solution was combined with an organic layer and washed with saturated saline. The organic layer was dried with magnesium sulfate, this mixture was naturally filtered, and the filtrate was concentrated. A solid obtained was purified by silica gel column chromatography (developing solvent; hexane:toluene=7:3). Recrystallization of the obtained solid with a mixed solvent of chloroform and hexane gave 514 mg of 9-[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-10-phenylanthracene (abbreviation: PCAPhA) as yellow powder in 67% yield.

Provenance & Evidence