Tris(1,1-dimethylethyl)phosphine → 9-{4-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]phenyl}-10-phenylanthracene

Participants

Reaction Conditions

Reaction Steps

2.0 g (5.0 mmol) of 9-phenyl-10-(4-bromophenyl)anthracene (PA), 1.9 g (5.0 mmol) of 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (PCN), 2.1 g (20 mmol) of t-butoxysodium (abbreviation: t-BuONa) were put in a 100 mL three neck flask, and nitrogen was substituted for air in the flask, and then 40 mL of toluene and 0.1 mL of tri(t-butyl)phosphine (10 wt % hexane solution) (abbreviation: P(tBu)3) were added, and the 100 mL three neck flask was depressurized and degassed. After degassing, 30 mg (0.05 mmol) of bis(dibenzylideneacetone)palladium(0) was added, and stirred for 3 hours at 80° C. After reaction, a reaction solution was washed with water and saturated saline in this order, and then an organic layer was dried with magnesium sulfate. After natural filtration, a solid which was obtained by concentrating the filtrate was purified with silica gel column chromatography (hexane:toluene=7:3). When a target substance was recrystallized with dichloromethane hexane, 1.5 g of a yellow-solid target substance was obtained in a yield of 43% (Synthesis Scheme (g-2)). This compound was measured by a nuclear magnetic resonance (NMR) method and confirmed to be was PCNPA.

Provenance & Evidence