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20 Compound 5:
IR (KBr): 2984, 1721, 1598, 1415, 1358, 1176, 907, 817, 663, 554
cm-¹. ¹H NMR (400
MHz, CDCl3): δ = 7.78
(d, J = 8.4
Hz, 4 H), 7.35 (d, J = 8.4
Hz, 4 H), 4.73 (d, J = 14.4
Hz, 4 H), 4.30-4.25 (m, 8 H), 4.04 (t, J = 5.2
Hz, 4 H), 2.90 (t, J = 5.2
Hz, 4 H), 2.48 (s, 6 H), 1.30 (t, J = 7.2 Hz,
6 H). ¹³C NMR (150 MHz, CDCl3): δ = 164.8,
158.3, 144.8, 132.5, 129.7, 127.7, 75.8, 67.2, 63.3, 59.7, 49.7,
21.4, 13.6. ESI-MS: m/z = 765.0 [M + H]+.
21 Compound 6:
IR (KBr): 2989, 2100, 1767, 1709, 1407, 1276, 899, 725 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 4.88 (d, J = 14.0 Hz,
4 H), 4.36 (d, J = 14.0
Hz, 4 H), 4.30 (q, J = 7.2
Hz, 4 H), 3.36 (t, J = 5.6
Hz, 4 H), 2.90 (t, J = 5.6
Hz, 6 H), 1.32 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 165.0,
158.4, 76.0, 63.4, 59.9, 50.4, 48.6, 13.8. ESI-MS: m/z = 506.2 [M]+.
26
General Procedure
for the Synthesis of Compound 7
The azide 6 (0.20 mmol) and arylacetylene (0.40 mmol) were
suspended in 1:1 mixture of H2O and t-BuOH
(10 mL). Ascorbate acid (0.020 mmol, 20 µL of freshly prepared
1.0 M solution in H2O, 10 mol%) was added, followed
by copper(II) sulfate pentahydrate (0.010 mmol, 100 µL
of 0.10 M solution in H2O, 5.0 mol%). The heterogeneous
mixture was stirred vigorously for 24 h under Ar protection. After total
consumption of the starting material (determination by TLC), the
solvent was removed in vacuo, and the residue was isolated by column
chromatography on SiO2 to get the pure product 7.
Compound 7a:
IR (KBr): 3244, 2985, 1705, 1444, 1282, 1047, 767, 697 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 7.86 (d, J = 7.6 Hz,
4 H), 7.60 (s, 2 H), 7.45 (t, J = 7.6
Hz, 4 H), 7.35 (t, J = 7.6
Hz, 2 H), 4.82 (d, J = 13.6
Hz, 4 H), 4.36 (t, J = 6.0
Hz, 4 H), 4.28 (q, J = 7.2
Hz, 4 H), 4.19 (d, J = 13.6 Hz,
4 H), 2.93 (t, J = 6.0
Hz, 4 H), 1.30 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.9,
158.6, 147.3, 130.6, 128.9, 128.1, 125.6, 120.3, 76.0, 63.5, 60.0,
50.1, 47.0, 13.8. ESI-HRMS: m/z [M + Na]+ calcd
for C34H38N12NaO6: 733.2929;
found: 733.2898.
Compound 7b:
IR (KBr): 3423, 3137, 2988, 1766, 1730, 1707, 1612, 1411, 1286,
1234, 1045, 907, 718 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 8.68
(d, J = 5.6
Hz, 4 H), 7.88 (s, 2 H), 7.77 (d, J = 5.6
Hz, 4 H), 4.81 (d, J = 13.6
Hz, 4 H), 4.45 (t, J = 5.2
Hz, 4 H), 4.31-4.22 (m, 8 H), 3.03 (t, J = 5.2 Hz,
4 H), 1.31 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.7,
158.5, 150.3, 144.9, 137.9, 122.0, 119.8, 75.9, 63.6, 59.9, 50.1,
47.6, 13.8. ESI-HRMS: m/z [M+Na]+ calcd
for C32H36N14NaO6: 735.2834;
found: 735.2814.
Compound 7c:
IR (KBr): 3447, 3134, 2939, 2840, 1760, 1718, 1459, 1299, 1248,
1231, 1027, 825, 717 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 7.78
(d, J = 8.4
Hz, 4 H), 7.50 (s, 2 H), 6.97 (d, J = 8.4
Hz, 4 H), 4.82 (d, J = 13.2
Hz, 4 H), 4.33-4.25 (m, 8 H), 4.18 (d, J = 13.2
Hz, 4 H), 3.80 (s, 6 H), 2.88 (t, J = 6.0
Hz, 4 H), 1.30 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.9,
159.5, 158.5, 147.2, 126.9, 123.3, 119.5, 114.2, 76.0, 63.5, 60.0,
55.2, 50.1, 46.8, 13.8. ESI-HRMS: m/z [M + Na]+ calcd
for C36H42N12NaO8: 793.3141;
found: 793.3100.
Compound 7d:
IR (KBr): 3448, 3367, 2982, 2849, 1720, 1621, 1502, 1416, 1291,
1233, 1029, 906, 837, 715 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 7.61
(d, J = 8.0
Hz, 4 H), 7.48 (s, 2 H), 6.68 (d, J = 8.0
Hz, 4 H), 4.79 (d, J = 13.6
Hz, 4 H), 4.28-4.24 (m, 8 H), 4.12 (d, J = 13.6
Hz, 4 H), 3.90 (br s, 4 H), 2.87 (t, J = 6.0
Hz, 4 H), 1.27 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.9,
158.5, 147.6, 146.7, 126.7, 120.6, 119.1, 115.1, 76.0, 63.5, 59.9,
50.0, 46.7, 13.8. ESI-HRMS: m/z [M + Na]+ calcd
for C34H40N14NaO6: 763.3147;
found: 763.3120.
Compound 7e:
IR (KBr): 3362, 3150, 2984, 2844, 1726, 1678, 1617, 1414, 1235,
1030, 982, 910, 858, 776, 713 cm-¹. ¹H
NMR (400 MHz, DMSO-d
6): δ = 8.50
(s, 2 H), 8.02 (s, 2 H), 7.98 (d, J = 8.0
Hz, 4 H), 7.91 (d, J = 8.0
Hz, 4 H), 7.42 (s, 2 H), 4.78 (d, J = 13.6
Hz, 4 H), 4.50 (t, J = 6.0
Hz, 4 H), 4.29-4.21 (m, 8 H), 3.01 (t, J = 6.0
Hz, 4 H), 1.21 (t, J = 7.2 Hz,
6 H). ¹³C NMR (100 MHz, DMSO-d
6): δ = 167.5,
164.9, 158.3, 145.4, 133.4, 133.3, 128.3, 124.8, 122.5, 75.8, 63.5, 59.3,
49.6, 46.9, 13.7. ESI-HRMS: m/z [M + Na]+ calcd
for C36H40N14NaO8: 819.3046;
found: 819.2999.
Compound 7f:
IR (KBr): 3423, 3137, 2988, 1766, 1730, 1707, 1612, 1411, 1286,
1234, 1045, 907, 718 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 8.43
(d, J = 8.0
Hz, 2 H), 7.82 (d, J = 8.0
Hz, 4 H), 7.70 (d, J = 8.0
Hz, 2 H), 7.55-7.47 (m, 8 H), 4.82 (d, J = 13.6
Hz, 4 H), 4.34 (t, J = 6.0
Hz, 4 H), 4.27 (q, J = 7.2
Hz, 4 H), 4.20 (d, J = 13.6
Hz, 4 H), 2.95 (t, J = 6.0
Hz, 4 H), 1.28 (t, J = 7.2
Hz, 6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.8,
158.5, 146.5, 133.7, 130.7, 128.8, 128.3, 127.8, 127.1, 126.7, 126.0,
125.4, 125.3, 122.9, 75.9, 63.5, 60.0, 50.2, 47.1, 13.8. ESI-HRMS: m/z [M + Na]+ calcd
for C42H42N12NaO6: 833.3242;
found: 833.3220.
Compound 7g:
IR (KBr): 3448, 3122, 2982, 1719, 1414, 1232, 1035, 906, 821, 712,
505, 488 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 7.47
(s, 2 H), 4.81-4.78 (m, 8 H), 4.34-4.30 (m, 8
H), 4.27 (q, J = 7.2
Hz, 4 H), 4.20 (d, J = 13.2
Hz, 4 H), 4.10 (s, 10 H), 2.94 (t, J = 5.6
Hz, 4 H), 1.29 (t, J = 7.2 Hz,
6 H). ¹³C NMR (100 MHz, CDCl3): δ = 164.9,
158.5, 146.4, 119.5, 76.0, 75.5, 69.6, 68.6, 66.5, 63.5, 60.0, 50.3, 47.1,
13.8. ESI-HRMS: m/z [M + Na]+ calcd
for C42H46Fe2N12NaO6:
949.2273; found:949.2215.
27
Crystal Data for
Compound 7a
C34H38N12O6, MW = 710.78,
triclinic, a = 10.0153
(5), b = 12.0495
(6), c = 16.3995
(8) Å, α = 102.658
(0)˚, β = 103.272
(0)˚, γ = 108.398 (0)˚, V = 1734.28
(15) ų, T = 294 (2) K, space
group Z = 4, m(MoKα) = 0.094
mm-¹, 15230 reflections measured, 6724
unique (Rint = 0.0981) which
were used in all calculations. The final wR
2 (F
2) was 0.1531. CCDC 699457
contains the supplementary crystallographic data for this paper.
These data can be obtained free of charge from The Cambridge Crystallographic
Data Centre via www.ccdc.cam.ac.uk/data_request/cif.