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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Copper immobilized on nano-silica triazine dendrimer 2 ) catalyzed synthesis of symmetrical and unsymmetrical 1,3-diynes under aerobic conditions and ambient temperature Mahboobeh Nasr-Esfahani, a Iraj Mohammadpoor-Baltork,* a Ahmad Reza Khosropour,* a Majid Moghadam, a Valliolah Mirkhani, a Shahram Tangestaninejad, a Vladislav Agabekov, b and Hadi Amiri Rudbari a] a Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan , Iran b Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104, Freiburg, Germany addresses: imbaltork@sci.ui.ac.ir; arkhosropour@sci.ui.ac.ir Table of Contents 1 Experimental Section S2 2 Spectroscopic data of the products 2a-2n (Table 2) and 3an-3dk (Table 4) S3-S8 3 1 H and 13 C NMR spectra of the products S9-S35 4 X-ray crystal structure of compound 3ad S36 5 Crystal data and structure refinement for compound 3ad S37 6 References S38 S1
2 1. Experimental Section Melting points were determined with a Stuart Scientific SMP2 apparatus. FT-IR spectra were recorded on a Nicolet-Impact 400D instrument in the range of cm H and 13 C NMR (400 and 100 MHz) spectra were recorded on a Bruker Avance 400 spectrometer using CDCl 3 as solvent. Mass spectra were recorded on a Platform II spectrometer from Micromass; EI mode at 70 ev. Elemental analysis was done on a LECO, CHNS-932 analyzer. The Cu content of the catalyst was measured by an inductively coupled plasma optical emission spectrometry (ICP-OES), using a Jarrell-Ash 1100 ICP analyzer. The Cu(II)- TD@nSiO 2 catalyst was prepared according to the reported procedure. 1 Typical procedure for synthesis of symmetrical 1,3-diyne 2a A mixture of phenylacetylene 1a (1 mmol), Cu(II)-TD@nSiO 2 (0.6 mol%), DBU (20 mol%) in acetonitrile (2 ml) was stirred under aerobic conditions at room temperature for 1.5 h. After completion of the reaction, as indicated by TLC (eluent: petroleum ether/ethyl acetate, 20:1), the catalyst was separated by centrifugation and washed with acetonitrile (5 ml). The solvent was evaporated and the residue was purified on a small bed of silica gel using petroleum ether/ethyl acetate (20:1) as eluent to afford the corresponding 1,3-diyne 2a in 99% yield. Typical procedure for synthesis of unsymmetrical 1,3-diyne 3an A mixture of phenylacetylene 1a (1 mmol) and ethyl propiolate 1n (0.5 mmol), Cu(II)- TD@nSiO 2 (0.6 mol%) and DBU (20 mol%) in acetonitrile (2 ml) was stirred under aerobic conditions at room temperature for 2 h. The progress of the reaction was monitored by TLC (eluent:petroleum ether/ethyl acetate, 20:1). After completion of the reaction, the catalyst was separated by centrifugation and washed with acetonitrile (5 ml). Evaporation of the solvent followed by purification of the crude product by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 20:1) afforded the desired unsymmetrical 1,3-diyne 3an in 89% yield. S2
3 2. Spectroscopic data of the products 2a-2n (Table 2) and 3an-3dk (Table 4): 1,4-Diphenylbuta-1,3-diyne (Table 2, 2a): 2 Yield 99%. Mp o C. IR (KBr): ν max = 3077, 2924, 2146, 1590, 1482, 914, 754, 684, 524 cm H NMR (400 MHz, CDCl 3 ): δ = 7.53 (dd, 1 J = 8.0, 2 J = 1.6 Hz, 4H), (m, 6H). MS: m/z (%): ([M+2] +, 2.40), ([M + ], 90.77), (34.87), (10.90), (43.08), (30.00), (36.92), (63.59), (73.33), (85.64), (100.00). 1,4-Bis(2-methoxyphenyl)buta-1,3-diyne (Table 2, 2b): 3 Yield 97%. Mp o C. IR (KBr): ν max = 3064, 3001, 2137, 1590, 1485, 1248, 1019, 753 cm H NMR (400 MHz, CDCl 3 ): δ = 7.42 (dd, 1 J = 7.6, 2 J = 1.6 Hz, 2H), 7.27 (td, 1 J = 7.6, 2 J = 1.6 Hz, 2H), 6.86 (dd, 1 J = 7.6, 2 J = 7.2 Hz, 4H), 3.82 (s, 6H). MS: m/z (%): ([M + ], 71.03), (15.10), (31.12), (30.11), (47.88), (27.10), (85.14), (100.00). 1,4-Bis(3-methoxyphenyl)buta-1,3-diyne (Table 2, 2c): 4 Yield 98%. Mp o C. IR (KBr): ν max = 3071, 2926, 2218, 1594, 1462, 1261, 1048, 782, 684 cm H NMR (400 MHz, CDCl 3 ): δ = 7.25 (t, J = 8.0 Hz, 2H), 7.13 (dt, 1 J = 8.0, 2 J = 1.2 Hz, 2H), 7.04 (dd, 1 J = 4.0, 2 J = 1.6 Hz, 2H), 6.94 (ddd, 1 J = 8.0, 2 J = 3.6, 3 J = 1.2 Hz, 2H), 3.80 (s, 6H). MS: m/z (%): ([M+1] +, 5.86), ([M + ], 37.11), (14.18), (15.21), (21.39), (21.39), (32.73), (34.28), (54.38), (100.00), (81.44). S3
4 1,4-Bis(4-methoxyphenyl)buta-1,3-diyne (Table 2, 2d): 2 Yield 99%. Mp o C. IR (KBr): ν max = 2999, 2929, 2134, 1597, 1500, 1250, 1023, 835, 534 cm H NMR (400 MHz, CDCl 3 ): δ = 7.47 (dt, 1 J = 8.4, 2 J = 2.4 Hz, 4H), 6.87 (dt, 1 J = 7.2, 2 J = 2.0 Hz, 4H), 3.82 (s, 6H). MS: m/z (%): ([M+1] +, 18.07), ([M + ], 89.11), (53.47), (18.32), (14.60), (33.17), (42.08), (21.78), (19.31), (32.18), (73.21), (100.00). 1,4-Bis(3,4,5-trimethoxyphenyl)buta-1,3-diyne (Table 2, 2e): 5 Yield 94%. Mp o C. IR (KBr): ν max = 3092, 2959, 2928, 2141, 1573, 1462, 1272, 1127, 992, 819, 712 cm H NMR (400 MHz, CDCl 3 ): δ = 7.71 (dd, 1 J = 8.4, 2 J = 3.2 Hz, 2H), 7.54 (dd, 1 J = 8.4, 2 J = 3.2 Hz, 2H), 3.87 (s, 6H), 3.86 (s, 12H). MS: m/z (%): ([M+2] +, 4.49), ([M+1] +, 22.18), ([M + ], ), (38.03), (6.56), (3.57), (12.15), (13.73), (29.23), (48.59), (73.94), (92.75). 1,4-Di-m-tolylbuta-1,3-diyne (Table 2, 2f): 2 Yield 98%. Mp o C. IR (KBr): ν max = 3033, 2917, 2138, 1645, 1591, 1478, 1038, 903, 787, 684 cm H NMR (400 MHz, CDCl 3 ): δ = 7.26 (s, 2H), 7.24 (s, 2H), 7.16 (d, J = 7.2 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 2.26 (s, 6H). MS: m/z (%): ([M+1] +, 19.72), ([M + ], ), (11.00), (7.79), (10.12), (20.42), (18.66), (50.70), (63.38), (67.61). S4
5 1,4-Di-p-tolylbuta-1,3-diyne (Table 2, 2g): 2 Yield 98%. Mp o C. IR (KBr): ν max = 3077, 2959, 2925, 2133, 1500, 1273, 1120, 809, 521 cm H NMR (400 MHz, CDCl 3 ): δ = 7.42 (d, J = 8.0 Hz, 4H), 7.14 (d, J = 8.0 Hz, 4H), 2.36 (s, 6H). MS: m/z (%): ([M+2] +, 1.23), ([M + ], 63.68), (12.15), (8.14), (6.57), (65.09), (97.17), (37.26), (50.94), (41.51), (84.43), (100.00), (96.23). 1,4-Bis(4-bromophenyl)buta-1,3-diyne (Table 2, 2h): 6 Yield 92%. Mp o C. IR (KBr): ν max = 3090, 2924, 1624, 1119, 824 cm H NMR (400 MHz, CDCl 3 ): δ = 7.50 (dt, 1 J = 8.4, 2 J = 2.0 Hz, 4H), 7.39 (dt, 1 J = 7.2, 2 J = 2.4 Hz, 4H). MS: m/z (%): ([M+4] +, 0.31), ([M+2] +, 0.54), ([M + ], 0.41), (0.55), (1.43), (6.27), (21.74), (6.52), (17.32), 69.13(27.45), (80.43), (100.00). 1,4-Bis(4-chlorophenyl)buta-1,3-diyne (Table 2, 2i): 5 Yield 94%. Mp o C. IR (KBr): ν max = 3084, 2929, 2141, 1590, 1110, 846, 530 cm H NMR (400 MHz, CDCl 3 ): δ = 7.46 (d, J = 7.6 Hz, 4H), 7.33 (d, J = 8.4 Hz, 4H). MS: m/z (%): ([M+2] +, 0.73), ([M + ], 0.41), (20.18), (43.12), (18.24), (21.11), (33.52), (17.32), (34.59), (68.54), (100.00). 1,4-Bis(4-vinylphenyl)buta-1,3-diyne (Table 2, 2j): Yield 90%. Mp o C. IR (KBr): ν max = 3097, 3054, 2939, 2124, 1643, 1594, 1020, 909, 540 cm H NMR (400 MHz, CDCl 3 ): δ = 7.42 (dd, 1 J = 8.4, 2 J = 2.0 Hz, 4H), 7.31 (d, J = 8.4 Hz, 4H), 6.66 (dd, 1 J = 10.8, 2 J = 6.8 Hz, 2H), 5.7 (dd, 1 J = 18.0, 2 J = 0.4 Hz, 2H), 5.26 (dd, 1 J = 10.8, 2 J = 0.4 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , S5
6 126.24, , , 82.01, MS: m/z (%): ([M+1] +, 11.40), ([M + ], 79.08), (10.11), (23.35), (21.44), (44.68), (50.94),, (82.41), (100.00), (76.23). Anal. Calcd for C 20 H 14 : C, 94.45; H, Found: C, H, ,4-Di(thiophene-2-yl)buta-1,3-diyne (Table 2, 2k): 2 Yield 97%. Mp o C. IR (KBr): ν max = 3100, 2920, 2198, 2136, 1617, 1220, 836, 710 cm H NMR (400 MHz, CDCl 3 ): δ = (m, 4H), 6.85 (t, J = 4.8 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , ,77.76, Tetradeca-6,8-diyne (Table 2, 2l): 7 Yield 86%. Oil. IR (KBr): ν max = 3050, 2964, 2936, 2219, 1473, 1362, 1150 cm H NMR (400 MHz, CDCl 3 ): δ = 2.19 (t, J = 7.2 Hz, 4H), 1.48 (quin, J = 7.2 Hz, 4H), (m, 8H), 0.84 (t, J = 7.2 Hz, 6H). MS: m/z (%): ([M] +, 0.96), (1.72), (28.08), (55.07), (100.00), (50.00), (42.93), (92.75). Dodeca-5,7-diyne (Table 2, 2m): 8 Yield 87%. Oil. IR (KBr): ν max = 2960, 2932, 2232, 1462, 1255, 1168 cm H NMR (400 MHz, CDCl 3 ): δ = 2.20 (t, J = 7.6 Hz, 4H), (m, 4H), (m, 4H), 0.85 (t, J = 7.2 Hz, 6H). O O O O Diethyl hexa-2,4-diynedioate (Table 2, 2n): 9 Yield 86%. Oil. IR (KBr): ν max = 2957, 2926, 2147, 1725, 1462, 1243, 1120, 739 cm H NMR (400 MHz, CDCl 3 ): δ = 4.28 (q, J = 7.2 Hz, 4H), 1.34 (t, J = 7.2 Hz, 6H). 13 C NMR (100 MHz, CDCl 3 ): δ = , 71.60, 67.09, 61.67, S6
7 Ethyl 5-phenylpenta-2,4-diynoate (Table 4, 3an): 10 Yield 89%. Oil. IR (KBr): ν max = 3066, 2926, 2226, 2149, 1737, 1602, 1214, 1071, 756, 690 cm H NMR (400 MHz, CDCl 3 ): δ = 7.48 (dd, 1 J = 8.0, 2 J = 1.2 Hz, 2H), 7.31 (td, 1 J = 7.6, 2 J = 1.6 Hz, 3H), 4.23 (q, J = 7.2 Hz, 2H), 1.28(t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , , , 78.64, 76.69, 62.47, 28.93, Methoxy-4-(phenylbuta-1,3-diyn-1-yl)benzene (Table 4, 3ad): 11 Yield 95%. Mp o C. IR (KBr): ν max = 3050, 2986, 2211, 2138, 1595, 1486, 1247, 1026, 826, 754 cm H NMR (400 MHz, CDCl 3 ): δ = 7.38 (dd, 1 J = 8.0, 2 J = 1.6 Hz, 2H), 7.34 (dt, 1 J = 8.4, 2 J = 2.0 Hz, 2H), 7.20 (m, 2H), 7.10 (s, 1H), 6.72 (dt, 1 J = 7.2, 2 J = 1.6 Hz, 2H), 3.67 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , , , , , 81.82, 81.03, 74.17, 72.74, ((4-Chlorophenyl)buta-1,3-diyn-1-yl)-3- methoxybenzene (Table 4, 3ci): Yield 93%. Mp o C. IR (KBr): ν max = 3064, 2955, 2211, 2151, 1591, 1248, 1036, 822, 777 cm H NMR (400 MHz, CDCl 3 ): δ = 7.48 (dt, 1 J = 8.4, 2 J = 2.0 Hz, 2H), 7.35 (dd, 1 J = 8.4, 2 J = 2.0 Hz, 2H), 7.28(d, J = 4.0 Hz, 1H),7.16 (dt, 1 J = 7.6, 2 J = 1.2 Hz, 1H), 7.07(dd, 1 J = 4.0, 2 J = 1.6 Hz, 1H), 6.97 (ddd, 1 J = 8.0, 2 J = 3.6, 3 J = 0.8 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , , , , , , , , 82.03, 80.33, 74.84, 74.84, 73.45, Anal. Calcd for C 17 H 11 ClO: C, 76.55; H, Found: C, 76.39; H, Methoxy-3-(octa-1,3-diyn-1-yl)benzene (Table 4, 3cm): 12 Yield 78%. Oil. IR (KBr): ν max = 3071, 2938, 2868, 2240, 2152, 1597, 1425, 1224, 1043, 781, S7
8 683 cm H NMR (400 MHz, CDCl 3 ): δ = 7.26 (t, J = 8.0 Hz, 1H), 7.10 (dt, 1 J = 7.6, 2 J = 1.2 Hz, 1H), 7.02 (dd, 1 J = 4.0, 2 J = 1.6 Hz, 1H), 6.93 (ddd, 1 J = 8.4, 2 J = 2.8, 2 J = 0.8 Hz, 1H), 3.81 (s, 3H), 2.40 (t, J = 7.6 Hz, 2H), (m, 2H), 1.53 (sex, J = 7.2, 2H), 0.97 (t, J = 7.2, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , , , , 84.93, 74.60, 74.20, 55.27, 30.27, 21.96, 19.28, ((4-Methoxyphenyl)buta-1,3-diyn-1-yl)thiophene (Table 4, 3dk): Yield 88%. Mp o C. IR (KBr): ν max = 3092, 2926, 2199, 2137, 1597, 1504,1290, 1250, 832, 710, 466 cm H NMR (400 MHz, CDCl 3 ): δ = 7.32 (dt, 1 J = 8.4, 2 J = 2.8 Hz, 2H), 7.17 (ddd, 1 J = 9.6, 2 J = 4.8, 2 J = 1.2 Hz, 1H), 7.10 (s, 1H), 6.84 (dd, 1 J = 5.2, 2 J = 3.6 Hz, 1H), 6.71(dt, 1 J = 6.8, 2 J = 2.4 Hz, 2H), 3.66 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ = , , , , , , , , 83.89, 78.21, 74.00, 68.16, Anal. Calcd for C 15 H 10 SO: C, 75.60; H, 4.23; S, Found: C, 75.47; H, 4.25; S, S8
9 2. 1 H and 13 C NMR spectra of the products: 1,4-Diphenylbuta-1,3-diyne (Table 2, 2a): 1 H NMR (400 MHz, CDCl 3 ) S9
10 1,4-Bis(2-methoxyphenyl)buta-1,3-diyne (Table 2, 2b): 1 H NMR (400 MHz, CDCl 3 ) S10
11 1,4-Bis(3-methoxyphenyl)buta-1,3-diyne (Table 2, 2c): 1 H NMR (400 MHz, CDCl 3 ) S11
12 1,4-Bis(4-methoxyphenyl)buta-1,3-diyne) (Table 2, 2d): 1 H NMR (400 MHz, CDCl 3 ) S12
13 1,4-Bis(3,4,5-trimethoxyphenyl)buta-1,3-diyne (Table 2, 2e): 1 H NMR (400 MHz, CDCl 3 ) S13
14 1,4-Di-m-tolylbuta-1,3-diyne (Table 2, 2f): 1 H NMR (400 MHz, CDCl 3 ) S14
15 1,4-Di-p-tolylbuta-1,3-diyne (Table 2, 2g): 1 H NMR (400 MHz, CDCl 3 ) S15
16 1,4-Bis(4-bromophenyl)buta-1,3-diyne (Table 2, 2h): 1 H NMR (400 MHz, CDCl 3 ) S16
17 1,4-Bis(4-chlorophenyl)buta-1,3-diyne (Table 2, 2i): 1 H NMR (400 MHz, CDCl 3 ) S17
18 1,4-Bis(4-vinylphenyl)buta-1,3-diyne (Table 2, 2j): 1 H NMR (400 MHz, CDCl 3 ) S18
19 1,4-Bis(4-vinylphenyl)buta-1,3-diyne (Table 2, 2j): 13 C NMR (100 MHz, CDCl 3 ) S19
20 1,4-Di(thiophene-2-yl)buta-1,3-diyne (Table 2, 2k): 1 H NMR (400 MHz, CDCl 3 ) S20
21 1,4-Di(thiophene-2-yl)buta-1,3-diyne (Table 2, 2k): 13 C NMR (100 MHz, CDCl 3 ) S21
22 Tetradeca-6,8-diyne (Table 2, 3l): 1 H NMR (400 MHz, CDCl 3 ) S22
23 Dodeca-5,7-diyne (Table 2, 2m): 1 H NMR (400 MHz, CDCl 3 ) S23
24 Diethyl hexa-2,4-diynedioate (Table 2, 2n): 1 H NMR (400 MHz, CDCl 3 ) S24
25 Diethyl hexa-2,4-diynedioate (Table 2, 2n): 13 C NMR (100 MHz, CDCl 3 ) S25
26 Ethyl 5-phenylpenta-2,4-diynoate (Table 4, 3an): 1 H NMR (400 MHz, CDCl 3 ) S26
27 Ethyl 5-phenylpenta-2,4-diynoate (Table 4, 3an): 13 C NMR (100 MHz, CDCl 3 ) S27
28 1-Methoxy-4-(phenylbuta-1,3-diyn-1-yl)benzene (Table 4, 3ad): 1 H NMR (400 MHz, CDCl 3 ) S28
29 1-Methoxy-4-(phenylbuta-1,3-diyn-1-yl)benzene (Table 4, 3ad): 13 C NMR (100 MHz, CDCl 3 ) S29
30 1-((4-Chlorophenyl)buta-1,3-diyn-1-yl)-3-methoxybenzene (Table 4, 3ci): 1 H NMR (400 MHz, CDCl 3 ) S30
31 1-((4-Chlorophenyl)buta-1,3-diyn-1-yl)-3-methoxybenzene (Table4, 3ci): 13 C NMR (100 MHz, CDCl 3 ) S31
32 1-Methoxy-3-(octa-1,3-diyn-1-yl)benzene (Table 4, 3cm): 1 H NMR (400 MHz, CDCl 3 ) S32
33 1-Methoxy-3-(octa-1,3-diyn-1-yl)benzene (Table 4, 3cm): 13 C NMR (100 MHz, CDCl 3 ) S33
34 2-((4-Methoxyphenyl)buta-1,3-diyn-1-yl)thiophene (Table 4, 3dk): 1 H NMR (400 MHz, CDCl 3 ) S34
35 2-((4-Methoxyphenyl)buta-1,3-diyn-1-yl)thiophene (Table 4, 3dk): 13 C NMR (100 MHz, CDCl 3 ) S35
36 Figure 1 X-ray crystal structure of compound 3ad. Thermal ellipsoids are drawn at the 30% probability level, while the hydrogen size is arbitrary. S36
37 Table 1 Crystal data and structure refinement for Compound 3ad. Empirical formula Temperature (K) Formula weight Wavelength Crystal system Space group Unit cell dimensions Volume Z Density (calculated) Absorption coefficient F(000) Theta range for data collection Index ranges Reflections collected Independent reflections Completeness to theta = Refinement method Data / restraints / parameters Goodness-of-fit on F 2 Final R indices [I>2sigma(I)] R indices (all data) Largest diff. peak and hole C 17 H 12 O 293(2) Ǻ Monoclinic P2(1)/c a = (2) Ǻ = 90 b = (19) Ǻ = (11) c = (15) Ǻ = (4) Ǻ Mg/m mm to <=h<=16, -11<=k<=11, -12<=l<= [R(int) = ] 100.0% Full-matrix least-squares on F / 0 / R1 = , wr2 = R1 = , wr2 = and e.ǻ 3 S37
38 References 1 M. Nasr-Esfahani, I. Mohammadpoor-Baltork, A. R. Khosropour, M. Moghadam, V. Mirkhani and S. Tangestaninejad, J. Mol. Catal. A: Chem, 2013, 379, R. Xiao, R. Yao and M. Cai, Eur. J. Org. Chem., 2012, S. Mehta and R. C. Larock, J. Org. Chem., 2010, 75, J. Park, E. Park, A. Kim, S.-A. Park, Y. Lee, K.-W. Chi, I. S. Kim and Y. H. Jung, J. Org. Chem., 2011, 76, E. Merkul, D. Urselmann and T. J. J. Mueller, Eur. J. Org. Chem., 2011, A. S. Abreu, P. M. T. Ferreira, M. R. P. Queiroz, E. Gatto and M. Venanzi, Eur. J. Org. Chem., 2004, X. Niu, C. Li, J. Li and X. Jia, Tetrahedron Lett., 2012, 53, D. Wang, J. Li, N. Li, T. Gao, S. Hou and B. Chen, Green Chem., 2010, 12, K. R. Deaton and M. S. Gin, Org. Lett., 2003, 5, Y. Liang, L.-M. Tao, Y. -H. Zhang and J.-H. Li, Synthesis, 2008, A. Dermenci, G. Dong and R. E. Whittaker, Org. Lett., 2013, 15, A. L. K. S. Shun, E. T.; Chernick, S. Eisler and R. R. Tykwinski, J. Org. Chem., 2003, 68, S38
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