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11 All new compounds were fully characterized
by 1H- and 13C NMR
spectroscopy, elemental analysis and/or HR-MS. Selected experimental procedures: Compound 6: To a solution of the phosphonium salt 5 (1.23 g, 2.42 mmol) in dry THF (40 mL)
at -78 ºC was slowly added n-BuLi
(1.6 m in hexane, 1.5 mL, 2.4 mmol), resulting
in a red solution. Then 4 (0.543 g, 1.10
mmol) in dry THF (15 mL) was slowly added. The resulting orange
solution was stirred at -78 ºC for 2 h, whereupon
sat aq NH4Cl (200 mL) was added. Then Et2O
(300 mL) was added, the organic phase was separated, dried (MgSO4),
and concentrated in vacuo. Column chromatography (SiO2,
CH2Cl2) afforded 6 (0.652
g, 66%) as an orange solid. Mp 155-156 °C. 1H
NMR (300 MHz, CDCl3): δ = 1.14 (s,
42 H), 3.84 (s, 6 H), 3.89 (s, 6 H), 7.55 (s, 4 H). 13C
NMR (75 MHz, CDCl3): δ = 11.3, 18.7,
53.3, 53.5, 101.6, 104.8, 107.7, 126.5, 129.6, 133.0, 135.4, 141.2, 159.4,
160.2. MALDI-TOF-MS [matrix: 2,5-dihydroxybenzoic acid
(DHB)]: m/z = 898
(M+). Elemental analysis: Calcd for C44H58O8S4Si2 (899.35):
C, 58.76; H, 6.50; S, 14.26; Found: C, 58.94; H, 6.38; S, 14.38. Compound 9
: To a solution
of 8 (126 mg, 0.12 mmol) in CH2Cl2 (10
mL) was added phenylacetylene (1 mL) and thereafter Hay catalyst
(1 mL) [Hay catalyst: CuCl (0.13 g, 1.3 mmol) and TMEDA
(0.16 g, 1.4 mmol) in CH2Cl2 (4.5 mL)].
The mixture was stirred for 20 min and then concentrated in vacuo
without heating. Column chromatography (SiO2, CH2Cl2/cyclohexane,
1:1) afforded 9 (89 mg, 60%) as
an orange oily solid. 1H NMR (300 MHz, CDCl3): δ = 0.88
(t, 6.6 Hz, 12 H), 1.27 (br s, 56 H), 1.66-1.74 (m, 8 H),
4.22 (t, 7.0 Hz, 4 H), 4.27 (t, 6.5 Hz, 4 H), 7.34-7.36 (m, 6 H),
7.53 (dd, 2.1/7.2 Hz, 4 H), 7.56 (s, 4 H). 13C
NMR (75 MHz, CDCl3): δ = 14.1, 22.7,
25.7, 25.8, 28.3, 29.1, 29.2, 29.3, 29.5 (× 2), 31.9, 67.0,
67.2, 73.8, 79.9, 83.6, 86.2, 105.4, 121.8, 126.9, 128.4, 129.2,
130.4, 132.3, 132.7, 135.4, 145.5, 158.9, 159.5. MALDI-TOF-MS (DHB): m/z = 1291 (M+).
HR-FT-MALDI-MS (DHB): Calcd for C78H98O8S4 (M+):
1290.6145; Found: 1290.6161. Compound 10: 8 (209 mg, 0.19 mmol) and 4-iodonitro-benzene
(490 mg, 1.97 mmol) were dissolved in dry THF (10 mL), and the mixture
was thoroughly Ar-degassed. Then [PdCl2(PPh3)2] (10
mg, 0.014 mmol) and diisopropylamine (1.5 mL) were added under Ar-degassing.
Finally, CuI (3 mg, 0.016 mmol) was added, and the mixture was stirred
for 3 h. Then Et2O (300 mL) was added, and the organic
phase was washed with H2O (250 mL) and saturated aqueous NH4Cl
(250 mL), dried (MgSO4), and concentrated in vacuo. Column
chromatography (SiO2, CH2Cl2/cyclohexane,
2:1) afforded 10 (74 mg, 29%)
as an orange oily solid. 1H NMR (300 MHz, CDCl3): δ = 0.88
(m, 12 H), 1.27 (br s, 56 H), 1.70-1.76 (m, 8 H), 4.24
(t, 6.8 Hz, 4 H), 4.29 (t, 6.5 Hz, 4 H), 7.62 (s, 4 H), 7.63 (d,
8.8 Hz, 4 H), 8.21 (d, 8.8 Hz, 4 H). 13C
NMR (75 MHz, CDCl3): δ = 14.1, 22.7,
25.7, 25.8, 28.3, 29.2 (× 2), 29.3, 29.5 (× 3),
31.9, 67.1, 67.3, 93.4, 97.3, 105.8, 123.7, 126.9, 129.8, 130.6,
131.6, 132.7, 135.5, 144.3, 146.9, 158.9, 159.5. HR-FT-MALDI-MS
(DHB): Calcd for C74H96N2O12S4:
1332.5846 (M+); Found: 1332.5833. Elemental
analysis: Calcd for C74H96N2O12S4 (1333.82):
C, 66.64; H, 7.25; N, 2.10; S, 9.61; Found: C, 66.84; H, 7.33; N,
2.15; S 9.55.
12
Hay AS.
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Org. Chem.
1962,
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3320
13
Sonogashira K. In
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Diederich F.
Stang PJ.
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14a
Hopf H.
Kreutzer M.
Jones PG.
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14b
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