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32. General experimental procedure for 1,3-diyne compounds 2a–j: A suspension of
alkynyl telluride (1a) (0.1435 g, 0.5 mmol), PdCl2 (0.08 g, 8 mmol %),
triethylamine (0.101 g, 1 mmol), and silver(I) acetate (0.083 g, 0.5 mmol) in
5 mL of methanol was irradiated in a water bath of an ultrasonic cleaner for
15 min. Then, the reaction was diluted with ethyl acetate (25 mL). The organic
layer was washed with a saturated solution of NH4Cl (2 ꢀ 10 mL) and water
(2 ꢀ 10 mL), dried over MgSO4, and concentrated under vacuum. The crude
product was purified by flash silica column chromatography using hexane as
the eluent and characterized as 1,4-diphenylbuta-1,3-diyne 2a:26 white solid;
mp 86–88 °C; 1H NMR (300 MHz, CDCl3) d 7.30–7.38 (m, 6H, ArH), 7.47–7.56
(m, 4H, ArH); 13C NMR (75.5 MHz, CDCl3) d 73.74, 81.34, 121.58, 128.43,
129.48, 132.29; GC–MS (%) 202 (100), 200 (24), 150 (8), 101 (13), 88 (10).
Compound 2b:27 white solid; mp 182–184 °C; 1H NMR (300 MHz, CDCl3) d 2.31
(s, 6H, 2Me), 7.09 (d, J = 8.0 Hz, 4H, ArH), 7.36 (d, J = 8.0 Hz, 4H, ArH); 13C NMR
(75.5 MHz, CDCl3) d 21.63, 73.45, 81.55, 118.80, 129.22, 132.40, 129.50; GC–
MS (%) 230 (100), 215 (17), 115 (17), 101 (15). Compound 2c:28 white solid; mp
90–92 °C; 1H NMR (300 MHz, CDCl3) d 0.89 (t, J = 6.8 Hz, 6H, 2Me), 1.27–1.38
(m, 8H, 4CH2), 1.53–1.66 (m, 4H, 2CH2), 2.60 (t, J = 7.6 Hz, 4H, 2CH2), 7.14 (d,
J = 8.0 Hz, 4H, ArH), 7.43 (d, J = 8.0 Hz, 4H, ArH); 13C NMR (75.5 MHz, CDCl3) d
13.78, 22.29, 30.63, 31.21, 35.74, 73.27, 81.36, 118.77, 128.33, 132.19, 144.28;
GC–MS (%) 342 (79), 285 (100), 228 (48). Compound 2d: white solid; mp 214–
216 °C; 1H NMR (300 MHz, CDCl3) d 3.92 (s, 6H, 2OMe), 7.09 (s, 2H, ArH), 7.16
(d, J = 9.0 Hz, 2H, ArH), 7.52 (d, J = 8.4 Hz, 2H, ArH), 7.68 (d, J = 8.4 Hz, 4H, ArH),
7.99 (s, 2H, ArH); 13C NMR (75.5 MHz, CDCl3) d 55.16, 74.25, 82.51, 105.66,
116.46, 119.41, 126.73, 128.12, 128.96, 129.21, 132.55, 134.36, 158.51; GC–MS
(%) 362 (100), 331 (76), 300 (46). Compound 2e:29 white solid, mp 60–62 °C;
1H NMR (300 MHz, CDCl3) d: 1.55–1.67 (m, 8H, 4CH2), 2.11–2.14 (m, 8H, 4CH2),
6.25 (t, J = 4.0 Hz, 2H); 13C NMR (75.5 MHz, CDCl3) d 21.3, 22.1, 25.8, 28.6, 71.5,
82.7, 119.9, 138.0, GC–MS (%): 210 (100) 181 (23), 167 (74), 153 (53), 128 (24),
115 (33), 91 (24), 77 (41). Compound 2f:30 colorless oil; 1H NMR (300 MHz,
CDCl3) d 0.96 (t, J = 7.2 Hz, 6H, 2Me), 1.45–1.59 (m, 4H, 2CH2), 2.20 (t, J = 6.8 Hz,
4H, 2CH2); 13C NMR (75.5 MHz, CDCl3) d 13.22, 20.93, 21.61, 65.14; GC–MS (%)
134 (39), 119 (32), 105 (41), 91 (100), 78 (45), 63 (28). Compound 2g:17
colorless oil; 1H NMR (300 MHz, CDCl3) d 0.92 (t, J = 7.2 Hz, 6H, 2Me), 1.26–
1.58 (m, 8H, 4CH2), 2.27 (t, J = 6.8 Hz, 4H, 2CH2); 13C NMR (75.5 MHz, CDCl3) d
13.29, 18.65, 21.68, 30.15, 65.00, 74.06; GC–MS (%) 162 (37), 147 (3), 133 (2),
119 (16), 91 (100), 78 (48). Compound 2h:29 Colorless oil; 1H NMR (300 MHz,
CDCl3) d 0.89 (t, J = 7.6 Hz, 6H, 2Me); 1.28–1.54 (m, 12H, 6CH2), 2.25 (t,
J = 7.2 Hz, 4H, 2CH2); 13C NMR (75.5 MHz, CDCl3) d 13.91, 19.23, 22.21, 28.04,
31.00, 65.21, 77.5; GC–MS (%) 190 (34), 161 (15), 105 (57), 91(100). Compound
2i:31 white solid; mp 106–108 °C; 1H NMR (300 MHz, CDCl3) d 0.17 (s, 18H,
19. For review: (a) Petragnani, N.; Stefani, H. A. Tetrahedron 2005, 61, 1613; (b)
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6Me); 13C NMR (75.5 MHz, CDCl3)
d
-0.34, 89.99, 93.04. Compound 2j:18
colorless oil; 1H NMR (300 MHz, CDCl3) d 3.40 (s, 6H, 2OMe), 4.17 (s, 4H, 2CH2);
13C NMR (75.5 MHz, CDCl3) d 57.60, 59.90, 70.24, 74.97.
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