2-(4-Chloro-phenylethynyl)-phenylamine

Synthesis

PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 mL) were added to an oven-dried, two-necked round-bottomed flask under standard reaction conditions. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 μL, 5.0 mmol) were sequentially added. The reaction mixture was degassed by argon bubbling for 15 min. Subsequently, 4-chlorophenylacetylene (300 μL, 2.75 mmol) was added and the reaction mixture was stirred at room temperature. The progress of the reaction was monitored by thin-layer chromatography (TLC), and after complete consumption of 2-iodoaniline (about 2 h), the reaction mixture was filtered through diatomaceous earth and the solvent was removed by rotary evaporation to obtain the crude product. The crude product was further purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/hexane (1:9, v/v) as eluent, resulting in purified 2-((4-chlorophenyl)alkynyl)-aniline (400 mg, 83% yield).

References

[1] Dalton Transactions, 2017, vol. 46, # 5, p. 1539 - 1545
[2] Tetrahedron Letters, 2014, vol. 55, # 40, p. 5495 - 5498
[3] Tetrahedron, 2011, vol. 67, # 46, p. 8918 - 8924
[4] Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 617 - 625
[5] Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10319 - 10328