Synthesis
GENERAL PROCEDURE: 2-Iodoaniline (500.2 mg, 2.28 mmol, 1.0 eq.) was dissolved in triethylamine (Et3N, 4.5 mL). To the resulting solution was added dichlorobis(triphenylphosphine)palladium(II) (PdCl2(PPh3)2, 32.1 mg, 0.046 mmol, 0.02 equiv) and cuprous iodide (CuI, 17.4 mg, 0.091 mmol, 0.04 equiv). The orange-colored solution was degassed by bubbling argon gas into the solution for 30 min at room temperature. After degassing, 4-ethynylanisole (0.30 mL, 279.0 mg, 2.73 mmol, 1.2 eq.) was added to the solution as a pure liquid via syringe. The resulting dark brown solution was stirred overnight at room temperature in an argon atmosphere. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate (NaHCO3). The aqueous phase was extracted (3 times) with ethyl acetate (EtOAc). The combined organic phases were washed sequentially with saturated aqueous sodium bicarbonate (SBC) and saturated aqueous sodium chloride (NaCl), and then dried over anhydrous sodium sulfate (Na2SO4). The crude product was obtained by filtration and concentration. The crude product was purified by silica gel (SiO2) column chromatography using 0-10% ethyl acetate-hexane gradient elution to afford 398.2 mg (90% yield) of (2-(4-methoxyphenyl)ethynyl)aniline as an orange solid.
References
[1] Dalton Transactions, 2017, vol. 46, # 5, p. 1539 - 1545
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[3] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 565 - 569
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 45, p. 11835 - 11839
[5] Angew. Chem., 2013, vol. 125, # 45, p. 12051 - 12055,5
