2-Aminobiphenyl → Biphenyl-4-yl- biphenyl-2-yl-amin;N-{[1,1'-biphenyl]-4-yl}-[1,1'-biphenyl]-2-amine

Participants

Reaction Steps

Xylene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (3.0 g, 7.2 mmol) and Pd2(dba)3 (1.6 g, 1.8 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (10.1 g, 60.0 mmol), 4-iodobiphenyl (16.8 g, 60.0 mmol), sodium tert-butoxide (11.5 g, 120.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 12 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using 30% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (18.3 g, 95% yield) as a white solid.

Provenance & Evidence