N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[Na+].CCCCCCCCCCCC.I[C:43]1[CH:44]=[C:45]([CH3:50])[CH:46]=[C:47]([CH3:49])[CH:48]=1>[Cu]I.O1CCOCC1>[CH3:50][C:45]1[CH:44]=[C:43]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)[CH:48]=[C:47]([CH3:49])[CH:46]=1
An oven-dried resealable Schlenk tube was charged with CuI (10 mg, 0.0525 mmol, 5.0 mol %), 1,10-phenanthroline (20 mg, 0.111 mmol), 4-cyanoaniline (146 mg, 1.24 mg), sodium tert-butoxide (145 mg, 1.51 mmol), evacuated and backfilled with argon. Dodecane (235 μL), 5-iodo-m-xylene (150 μL, 1.04 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting brown suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 5:1; 10 mL fractions). Fractions 7-16 provided 159 mg (69% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 7.51-7.47 (m, 2H), 6.91-6.95 (m, 2H), 6.83-6.80 (m, 2H), 6.80-6.78 (m, 1H), 6.02 (br s, 1H), 2.33 (q, J=0.5 Hz, 6H).
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