I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[NH4+].[OH-]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:9]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1)#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]To a mixture of 4-iodoaniline (2.19 g, 10 mmol), CuI (38 mg, 0.2 mmol, 2 mol %) and Pd(PPh3)2Cl2 (70 mg, 0.1 mmol, 1 mol %) under argon was added THF (60 mL), followed by non-1-yne (1.49 g, 12 mmol, 1.2 equiv.). After stirring for 1 min at rt, 0.5 M NH4OH (40 mL) was added dropwise. After addition, the resulting mixture was stirred 0/N at rt. It was extracted with ether (60 mL+30 mL) and combined extracts were dried (Na2SO4) and purified by flash chromatography (eluent: EtOAc/Hex=1:6) to give 4-(non-1-ynyl) aniline as a light yellow oil (1.85 g, 86%). 1H NMR (400 MHz, CDCl3) δ 7.22 (d, 2H, J=8.4 Hz), 6.60 (d, 2H, J=8.4 Hz), 3.65 (s, br, 2H, NH2), 2.38 (t, 2H, J=7.0 Hz), 1.59 (quint, 2H, J=7.2 Hz), 1.44 (quint, 2H, J=6.8 Hz), 1.38-1.25 (m, 6H), 0.90 (t, 3H, J=6.4 Hz).
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