Chemical Papers
(400 MHz, CDCl3) δ 7.91 (d, J=8.0 Hz; 1H), 7.77-7.70 (m,
2H), 7.48–7.34 (m, 3H), 7.16–7.10 (m, 1H), 3.70 (s, 1H);
13C NMR (100 MHz, CDCl3) δ 141.4, 140.1, 136.9, 136.0,
127.7, 127.4, 127.1, 125.7, 125.4, 123.2, 122.1, 111.8, 85.8,
78.3; IR (ATR) vmax (cm−1): 3286, 3101, 2922, 2851, 2095,
1940, 1791, 1438, 1189, 752, 690, 647, 584; HRMS calcd
for C14H9S2, 241.0146 [M+H]+ found; 241.0139 [M+H]+
127.01, 125.6, 125.2, 123.3, 122.1, 120.4, 113.1, 98.2, 83.6,
21.8; IR (ATR) vmax (cm−1): 3069, 2981, 2918, 1437, 807,
752; HRMS: calcd for C21H15S2, 331.0615 [M+H]+ found
331.0699 [M+H]+.
Compound 14C
The terminal alkyne (13), 170 mg (0.7 mmol), dimeth-
ylformamide (DMF) (7.5 mL), 4-iodoaniline, 153 mg
(0.75 mol), triethylamine (3.0 mL), PdCl2(PPh3)2, 24.5 mg
(0.035 mmol), and CuI, 7 mg (0.035 mmol) were employed
to aford 55% yield as yellow solid of the indicated prod-
General procedure of Sonogashira cross‑coupling
reaction between compound 13 and aryl iodide
(14A–H)
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uct. H NMR (400 MHz, CDCl3) δ 7.98 (d, J = 10.0 Hz;
To a stirred mixture of the terminal alkyne 13 (0.7 mol),
dimethylformamide (DMF) (7.5 mL), aryl iodide com-
pound (0.75 mol), triethylamine (3.0 mL), PdCl2(PPh3)2
(0.035 mol) under argon atmosphere CuI was added
(0.035 mmol). The resulting mixture was stirred at room
temperature for 10 h. Then, the reaction mixture was
quenched with water (30 mL) and extracted with EtOAc
(3 × 30 mL). The organic layer was dried over anhydrous
MgSO4 and fltered. The solvent was removed under vac-
uum, and the residue was purifed by column chromatogra-
phy over silica gel with Hexane–EtOAc.
1H), 7.76 (d, J=9.6 Hz; 1H), 7.65 (dd, J=3.7 Hz, 1.12 Hz;
1H), 7.51 (d, J=8.7 Hz; 2H), 7.47–7.35 (m, 3H), 7.14–7.11
(m, 1H), 6.70 (d, J=8.7 Hz; 2H), 3.9 (brs, 2H). 13C NMR
(100 MHz, CDCl3) δ 147.2, 140.9, 138.8, 136.9, 136.8,
133.2, 127.4, 126.8 (including 2C), 125.6, 125.2, 123.4,
122.1, 115.1, 113.6, 112.8, 98.9, 82.2; IR (ATR) vmax (cm−1):
3648, 3378.68, 2956, 2922, 2194, 1603, 1614, 1288, 1174,
906, 825, 729, 696; HRMS:calcd for C20H14S2, 332.0568
[M+H]+ found 332.0559 [M+H]+.
Compound 14D
Compound 14A
The terminal alkyne (13), 170 mg (0.7 mol), dimethyl-
formamide (DMF) (7.5 mL), 2-iodothioanisole, 175 mg
(0.75 mol), triethylamine (3.0 mL), PdCl2(PPh3)2, 24.5 mg
(0.035 mol), and CuI, 7 mg (0.035 mmol) were employed
to aford 93% yield as yellow solid of the indicated product.
1H NMR (400 MHz, CDCl3) δ 8.16 (d, J = 8.0 Hz; 1H),
7.75 (d, J = 7.96 Hz; 1H) 7.72 (dd, J = 3.7 Hz, 1.08 Hz;
1H), 7.66 (dd, J = 7.7 Hz, 1.32 Hz;1H), 7.49–7.33 (m,
4H) 7.27–7.24 (m, 1H), 7.22–7.11 (m, 2H),2.56 (s, 3H);
13C NMR (100 MHz, CDCl3) δ 141.7, 141.0, 136.9, 136.5,
132.64, 130.0, 129.2, 127.6, 127.3, 127.2, 125.7, 125.5,
124.6, 124.5, 123.8, 122.1, 121.7, 113.0, 95.1, 90.5, 15.52;
IR (ATR) vmax (cm−1): 3054, 2919, 2197, 1433, 1069, 745,
691; HRMS: calcd for C21H15S3, 363.0336 [M+H]+ found
363.0335 [M+H]+.
The terminal alkyne (13) 170 mg (0.7 mol), dimethylforma-
mide (DMF) (7.5 mL), iodobenzene, 142.8 mg (0.75 mol),
triethylamine (3.0 mL), PdCl2(PPh3)2, 24.5 mg (0.035 mol),
and CuI 7 mg (0.035 mmol) were employed to aford 68%
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yield as yellow-green solid of the indicated product. H
NMR (400 MHz, CDCl3) δ 7.99 (d, J=7.4 Hz; 1H), 7.77 (d,
J=8.0 Hz; 1H), 7.74–7.70 (m, 2H), 7.66 (d, J=3.7 Hz; 1H),
7.49–7.37 (m, 6H), 7.13–7.15 (m, 1H). 13C NMR (100 MHz,
CDCl3) δ 140.8; 140.2, 137.0, 136.5, 131.8, 128.8, 128.7,
127.5, 127.2, 127.16, 125.7, 125.3, 123.5, 123.3, 122.2,
113.0, 97.9, 84.2; IR (ATR) vmax (cm−1): 3063, 2980, 2922,
2199, 1438, 1237, 746, 684; HRMS: calcd for C20H13S2,
317.0419 [M+H]+ found, 317.0457 [M+H]+.
Compound 14B
Compound 14E
The terminal alkyne (13), 170 mg (0.7 mol), dimethyl-
formamide (DMF) (7.5 mL), 4-iodotoluene, 152.6 mg
(0.75 mol), triethylamine (3.0 mL), PdCl2(PPh3)2, 24.5 mg
(0.035 mol), and CuI, 6.66 mg (0.035 mmol) were employed
to aford 80% yield as yellow solid of the indicated product.
1H NMR (400 MHz, CDCl3) δ 7.98 (d, J = 8.0 Hz; 1H),
7.76 (d, J=7.9 Hz; 1H), 7.66 (d, J=3.8 Hz; 1H), 7.60 (d,
J=8.0 Hz; 2H), 7.48–7.36 (m, 3H), 7.24 (d, J=7.9 Hz; 2H),
7.15–7.12 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 140.8,
139.8, 139.0, 137.0, 136.6, 131.7, 129.5, 127.4, 127.04,
The terminal alkyne (13), 170 mg (0.7 mol), dimethylforma-
mide (DMF) (7.5 mL), 4-iodoanisole, 163 mg (0.75 mol),
triethylamine (3.0 mL), PdCl2(PPh3)2 (24.5 mg, 0.035 mol),
and CuI 7 mg (0.035 mmol) were employed to aford 80%
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yield as yellow-green solid of the indicated product. H
NMR (400 MHz, CDCl3) δ 7.98 (d, J=10.2 Hz; 1H), 7.76
(d, J=7.9 Hz, 1H), 7.66–7.63 (m, 3H), 7.45–7.35 (m, 3H),
7.14–7.11 (m, 1H), 6.96 (d, J=14.4 Hz, 2H), 3.87 (s, 3H).
13C NMR (100 MHz, CDCl3) δ 160.0, 140.8, 139.4, 136.9,
136.7, 133.3, 127.4, 127.0, 126.9, 125.6, 125.2, 123.4,
1 3