4-Aminobenzonitrile → 4-Cyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline

Participants

Reaction Steps

9.0 g of carbazole from step (2b) above and 2.23 g 4-aminobenzonitrile were mixed in 60 mL toluene in nitrogen filled glove box. 0.4 g Pd2DBA3 and 0.18 g tri-t-butylphosphine were added followed quickly by 1.81 g t-BuONa. The mixture was heated briefly to reflux then held at 80° C. overnight in the glove box with vigorous stirring. After cooling the reaction was chromatographed on silica using a gradient of DCM:hexanes (1:4 to 4:1) to elute the product which upon concentration and addition of hexanes precipitated the desired product in ˜80% yield (˜6.5 g) with structure confirmed by 1-H nmr spectroscopy.

Provenance & Evidence