Aniline → N-Phenyl-4-(trimethylsilyl)aniline

Participants

Reaction Conditions

Reaction Steps

Aniline (127.5 m mol)), (4-bromophenyl)trimethylsilane (102 m mol)), tris(dibenzylideneaceton)dipalladium(O) (1.53 m mol)), BINAP(2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.06 m mol)), and sodium-tert-butoxide (132.6 m mol)) were dissolved in toluene (100 ml) in a 250 ml tri-neck-round bottom flask and then stirred in a bath of 100° C. for 24 hours. After the reaction was terminated, the toluene was removed from the solution. After extraction was performed on the solution using dichloromethane and water, the resulting solution was reduced in pressure and distilled. After a silica gel column chromatography, the solvent was reduced in pressure and distilled, thereby obtaining 4-(trimethylsilyl)-N-phenylbenzeneamine liquid having 0.3 g.

Provenance & Evidence