Cul-catalyzed homocoupling of terminal alkynes to 1,3-diynes
1,4-Bis(4-n-propylphenyl) buta-1,3-diyne (2c)
Eicosa-9,11-diyne (2l)[9i]
White solid. M.p. 108–109 ◦C (lit.[15] 107.6 ◦C); 1H NMR (CDCl3,
500 MHz) δ 7.44 (d, J = 8.0 Hz, 4H), 7.14 (d, J = 8.0 Hz, 4H), 2.59
(t, J = 7.5 Hz, 4H), 1.62 (m, 4H), 0.94 (t, J = 7.5 Hz, 6H); 13C NMR
(CDCl3, 125 MHz) δ 144.4, 132.5, 128.8, 119.2, 81.7, 73.6, 38.2, 24.4,
13.9; MS: m/z (%) 286 (M+, 57).
Colorless oil; 1H NMR (CDCl3, 500 MHz) δ 2.23 (t, J = 7.5 Hz, 4H),
1.53–1.26 (m, 24H), 0.87 (t, J = 7.5 Hz, 6H); 13C NMR (CDCl3,
125 MHz) δ 77.6, 65.4, 31.9, 29.3, 29.2, 28.9, 28.5, 22.8, 19.3, 14.2.
1,4-Bis(cyclohex-1-enyl)buta-1,3-diyne (2m)
White solid. M.p. 64–66 ◦C (lit.[9i] 63–65 ◦C). 1H NMR (CDCl3,
500 MHz) δ 6.25 (t, J = 4.0 Hz, 2H), 2.03–2.01 (m, 8H), 1.65–1.54
(m, 8H); 13C NMR (CDCl3, 125 MHz) δ 138.2, 120.0, 82.8, 71.6, 28.8,
25.9, 22.2, 21.4.
1,4-Bis(4-n-pentylphenyl) buta-1,3-diyne (2d)
White solid. M.p. 83–84 ◦C (lit.[9j] 85–86 ◦C); 1H NMR (CDCl3,
500 MHz) δ 7.43 (d, J = 8.5 Hz, 4H), 7.14 (d, J = 8.0 Hz, 4H),
2.60 (t, J = 7.5 Hz, 4H), 1.63–1.56 (m, 4H), 1.36–1.25 (m, 8H), 0.89
(t, J = 7.0 Hz, 6H); 13C NMR (CDCl3, 125 MHz) δ 144.6, 132.5, 128.7,
119.1, 81.7, 73.6, 36.1, 31.6, 31.0, 22.7, 14.2; MS: m/z (%) 342 (M+,
100).
Acknowledgments
We thank the National Natural Science Foundation of China
(nos 20872087 and 20902057), the Key Laboratory of Synthetic
Chemistry of Natural Substances, Chinese Academy of Sciences,
Leading Academic Discipline Project of Shanghai Municipal
Education Commission (no. J50101) and the Innovation Fund
of Shanghai University for financial support.
1,4-Bis(4-methoxylphenyl) buta-1,3-diyne (2e)
White solid. M.p. 138–139 ◦C (lit.[9i] 138–140 ◦C); 1H NMR (CDCl3,
500 MHz) δ 7.46 (d, J = 8.5 Hz, 4H), 6.85 (d, J = 8.5 Hz, 4H), 3.82
(s, 6H); 13C NMR (CDCl3, 125 MHz) δ 160.3, 134.1, 114.2, 113.9, 81.4,
73.1, 55.4; MS: m/z (%) 262 (M+, 100).
Supporting information
1,4-Bis(4-fluorophenyl) buta-1,3-diyne (2f)
Supporting information may be found in the online version of this
article.
White solid. M.p. 193 ◦C (lit.[16] 190–191 ◦C); 1H NMR (CDCl3,
500 MHz) δ 7.53–7.49 (m, 4H), 7.04 (t, J = 8.5 Hz, 4H); 13C
NMR (CDCl3, 125 MHz) δ 164.2, 162.2, 134.7, 134.6, 118.0, 117.9,
116.1, 116.0, 80.6, 73.7; 19F NMR (CDCl3, 470.5 MHz) δ −108.430,
−108.449, −108.459, −108.466, −108.471, −108.478, −108.488;
MS: m/z (%) 238 (M+, 100).
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Colorless oil; 1H NMR (CDCl3, 500 MHz) δ 2.23 (t, J = 7.0 Hz, 4H),
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White solid. M.p. 128–129 ◦C (lit.[9i] 128–130 ◦C); 1H NMR (CDCl3,
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White solid. M.p. 38–39 ◦C (lit.[18] 39 ◦C); 1H NMR (CDCl3, 500 MHz)
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Hexa-2,4-diyne-1,6-diol (2k)
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c
Appl. Organometal. Chem. 2011, 25, 16–20
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