Tris(1,1-dimethylethyl)phosphine → N-(biphenyl-4-yl)-N-(4-tert-butylphenyl)chrysene-3-amine

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Reaction Steps

In a drybox, 3-bromochrysene (0.869 g, 2.83 mmol) and N-(4-tert-butylphenyl)biphenyl-4-amine (0.9 g, 2.97 mmol) were combined in a thick-walled glass tube and dissolved in 20 ml of dry o-xylene. Tris(tert-butyl)phosphine (0.01 g) and tris(dibenzylideneacetone) dipalladium(0) (0.023 g) were dissolved in 10 ml of dry o-xylene and stirred for 10 minutes. The catalyst solution was added to the reaction mixture, stirred for 5 minutes and followed by sodium tert-butoxide (0.27 g, 2.83 mmol) and 25 ml of dry o-xylene. After another 10 minutes, the reaction flask was brought out of the drybox, attached to a nitrogen line and stirred at 75° C. overnight. Next day, reaction mixture was cooled to room temperature and filtered through a one-inch plug of silica gel and one inch of celite, washing with dichloromethane. Removal of volatiles under reduced pressure gave a solid which was triturated with diethyl ether. Yield 1.27 g (85.2%). Identity of the product was established by 1H NMR. The compound properties are given in Table 1.

Provenance & Evidence