Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC([O-])(C)C.[Na+]>O1CCOCC1>[C:2]1([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Following general procedure F, a mixture of chlorobenzene (51 μL, 0.5 mmol), N1-phenylbutane-1,4-diamine (98 mg, 0.6 mmol), NaOt-Bu (97 mg, 1.0 mmol), 10 (4 mg, 1 mol %), 1 (2.5 mg, 1 mol %), and dioxane (0.5 mL) was heated to 80° C. for 2 h. The crude product was purified via the Biotage SP4 (silica-packed 50 g snap; 0-75% EtOAc/hexanes) to provide the title compound as a clear oil (108 mg, 91%). 1H NMR (300 MHz, CDCl3) δ: 7.28 (t, J=7.0 Hz, 4H), 6.80 (t, J=7.0 Hz, 2H), 6.68 (d, J=7.0 Hz, 4H), 3.68 (s, 2H), 3.22 (m, 4H), 1.78 (m, 4H) ppm. 13C NMR (75 MHz, CDCl3) δ: 148.6, 129.6, 117.6, 113.1, 44.0, 27.4 ppm. IR (neat, cm−1): 3407, 3050, 2934, 2861, 1603, 1507, 1477, 1321, 1257, 1179, 749, 693. Anal. Calcd. for C16H20N2: C, 79.96; H, 8.39. Found: C, 80.20; H, 8.48.
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