4-Bromotoluene → 4-[2-(4-Methylphenyl)ethenyl]-N,N-diphenylaniline

Participants

Reaction Conditions

Reaction Steps

An oven dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd2dba3 (2 mol %) and NaO-t-Bu (3.5 mmol). The tube was capped with a rubber septum, evacuated and then flushed with argon three times. P(isoBuNCH2CH2)3N (4 mol %), 4-aminostyrene (1 mmol), bromobenzene (314 mg, 2 mmol) and toluene (10 mL) were successively added via syringe. After the tube was heated at 60° C. for 3 h, all the starting material was converted in to the N,N-diphenylaminostyrene as judged by TLC. To this reaction mixture, 4-bromotoluene (205 mg, 1.2 mmol) was added and the temperature was raised to 110° C. After heating for another 16 h, the reaction mixture was cooled to room temperature. The reaction mixture was filtered through a celite pad to remove the solid impurities and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography using 1% EtOAc/hexane as eluants to afford the coupled product (6), namely N,N-diphenyl-4-[2-(4-methylphenyl) ethenyl]benzenamine (312 mg, 86%) as a yellow solid (See Entry 1 of Table 3).

Provenance & Evidence