2-Aminobiphenyl → N-([1,1'-biphenyl]-2-yl)-N-(4-methoxyphenyl)-[1,1'-biphenyl]-2-amine

Participants

Reaction Steps

Toluene (100 mL) was bubbled with nitrogen for 15 min, followed by the addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.0 g, 2.4 mmol) and Pd2(dba)3 (0.5 g, 0.6 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 2-iodobiphenyl (3.5 mL, 20.0 mmol), and sodium tert-butoxide (3.8 g, 40.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 21 h. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% DCM/hexane. The solvent was removed in vacuo. The residue was dissolved in 1,2-dichlorobenzene (80 mL). After that, 4-iodoanisole (18.7 g, 80.0 mmol), potassium carbonate (5.5 g, 40.0 mmol), copper powder (1.3 g, 20.0 mmol), and 18-crown-6 ether (5.3 g, 20.0 mmol) were added. The resultant mixture was bubbled with nitrogen for 30 min. The mixture was refluxed for 88 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane to yield N-([1,1′-biphenyl]-2-yl)-N-(4-methoxyphenyl)-[1,1′-biphenyl]-2-amine (7.4 g, 87% yield) as a colorless oil.

Provenance & Evidence