Reusable Cu 2 O/PPh 3 /TBAB System for the Cross-Couplings of Aryl Halides and Heteroaryl Halides with Terminal Alkynes. Supporting Information
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1 Reusable Cu 2 O/PPh 3 /TBAB System for the Cross-Couplings of Aryl Halides and Heteroaryl Halides with Terminal Alkynes Bo-Xiao Tang, Feng Wang, Jin-Heng Li,* Ye-Xiang Xie, and Man-Bo Zhang* Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha , China jhli@hunnu.edu.cn Supporting Information List of Contents (A) Remarks S2 (B) Typical experimental procedure S2-3 (C) Analytical data for 3-16, and 24 S3-9 (D) References S9-10 (E) Spectra S11-52 S1
2 (A) Remarks There shapes of Cu 2 O nanoparticles including cubic Cu 2 O nanoparticles, octahedral Cu 2 O nanoparticles and spherical Cu 2 O nanoparticles were prepared by known 1 procedures. (B) Typical experimental procedure Typical experimental procedure for the Cu 2 O/PPh 3 /TBAB (n-bu 4 NBr) system for the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes. A mixture of aryl halide 1 (0.5 mmol), alkyne 2 (0.7 mmol), pyramid-like Cu 2 O nanoparticles (10 mol %), PPh 3 (L2; 20 mol%), K 2 CO 3 (2 equiv) and TBAB (1.5 g) was stirred at o C for desired time (indicated in Table 2) until complete consumption of starting material as monitored by TLC. After the reaction was finished, diethyl ether was poured into the mixture, then washed with water, extracted with diethyl ether, dried by anhydrous Na 2 SO 4 and evaporated under vacuum, the residue was purified by flash column chromatography (hexane or hexane/ethyl acetate) to afford the desired coupled product. After initial experimentation, the residue (the Cu 2 O nanoparticles/pph 3 /TBAB system) was then solidified (evaporated in vacuo and cooled) and subjected to a second run of the Sonogashira reaction by charging with the same substrates (aryl halide, alkyne and K 2 CO 3 ). Octahedral Cu 2 O nanoparticles preparation. 2.4 ml of 6 M NaOH was droped slowly to a mixture of PEG (400 mg), CuCl 2 (540 mg) and distilled H 2 O. After S2
3 the mixture was stirred for 20 min, 2.5 ml of M N 2 H 4 H 2 O was droped slowly to give red precipitates Cu 2 O. Then the Cu 2 O precipitates were isolated by centrifuge, and washed with distilled water (5 5 ml), anhydrous ethanol (3 5 ml) and acetone (3 5 ml). Finally, the collected Cu 2 O precipitates were dried in a vacuum oven at 60 o C to offer the Octahedral Cu 2 O nanoparticles (210 mg). Cubic Cu 2 O nanoparticles preparation. A mixture of PEG-6000 (300 mg), Cu(OAc) 2 H 2 O (399 mg) and D-(+)-glucose (1800 mg) was dissolved in water (100 ml). The mixture was stirred at 50 o C to ensure them dissolved completely, followed by dropwise addition of NaOH (5 M, 2 ml) into the solution. After the solution was stirred at 50 o C for 40 min, the Cu 2 O precipitate was isolated by centrifuge, then washed with distilled water, ethanol and acetone in turn, and dried in a vacuum oven at 40 o C to offer Cu 2 O nanoparticles (110 mg). Spherical Cu 2 O nanoparticles preparation. Cu(OAc) 2 H 2 O (399 mg; 2 mmol) was dissolved in 25 ml of DMF, followed by the addition of poly(vinyl pyrrolidone) (PVP; 05-2-mmol; molecular weight = 30,000) and NaBH 4 ( g). After stirring for several minutes, the mixture was heated at 90 o C, and in 2-6 min, the color of the mixture was an orange color. The mixture was cooled to room temperature at once and washed by alcohol several times to give Cu 2 O nanoparticles (93 mg). (A) Analytical data for 3-16, and 24 S3
4 1-(2-(4-Nitrophenyl)ethynyl)benzene (3): 2 1 H NMR (400 MHz, CDCl 3 ) δ: 8.23 (d, J = 8.8 Hz, 2H), 7.67 (d, J = 8.8 Hz, 2H), 7.57 (d, J = 9.2 Hz, 2H), 7.39 (t, J = 7.6 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ: 141.3, 132.6, 132.2, 130.6, 129.6, 128.8, 124.0, 122.5, 95.0, 87.9; LRMS (EI, 70 ev) m/z (%): 223 (M +, 100). 1,2-Diphenylethyne (4): 2 1 H NMR (300 MHz, CDCl 3 ) δ: (m, 4H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ: 132.0, 128.7, 128.6, 123.7, 89.7; LRMS (EI, 70 ev) m/z (%): 178 (M +, 100). 1-(Hept-1-ynyl)benzene (5): 2 1 H NMR (400 MHz, CDCl 3 ) δ: 7.41 (d, J = 8.0 Hz, 2H) 7.28 (t, J = 5.2 Hz, 3H), 2.42 (t, J = 7.2 Hz, 2H), (m, 2H), (m, 4H), 0.94 (t, J = 7.2 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 131.6, 128.2, 127.5, 124.1, 90.5, 80.6, 31.2, 28.5, 22.3, 19.4, 14.0; LRMS (EI, 70 ev) m/z (%): 172 (M +, 13), 143 (28), 129 (30), 128 (33), 115 (100). 4-Phenylbut-3-yn-1-ol (6): 3 1 H NMR (400 MHz, CDCl 3 ) δ: 7.41 (d, J = 8.0 Hz, 2H), 7.29 (t, J = 6.2 Hz, 3H), 3.81 (t, J = 6.4 Hz, 2H), 2.68 (t, J = 6.6 Hz, 2H), 2.33 (brs, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ: 131.6, 18.3, 128.0, 123.4, 86.5, 82.4, 61.2, 23.8; LRMS (EI, 70 ev) m/z (%): 146 (M +, 11), 128 (-OH, 5), 116 (37), 115 (100). S4
5 1-(2-o-Tolylethynyl)benzene (7): 4 1 H NMR (400 MHz, CDCl 3 ) δ: (m, 3H), (m, 4H), (m, 2H) 2.52 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 140.2, 132.6, 131.9, 131.6, 129.5, 129.2, 128.4, 128.3, 128.2, 125.6, 88.4, 81.7, 20.7; LRMS (EI, 70 ev) m/z (%): 192 (M +, 100). 1-Methoxy-4-(2-phenylethynyl)benzene (8): 2 1 H NMR (400 MHz, CDCl 3 ) δ: (m, 4H), (m, 3H), 6.88 (d, J = 8.8 Hz, 2H), 3.83 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 159.6, 133.0, 131.4, 128.3, 127.9, 123.6, 115.4, 114.0, 89.4, 88.1, 55.3; LRMS (EI, 70 ev) m/z (%): 208 (M +, 100). 1-(Hept-1-ynyl)-4-methoxybenzene (9): 2 1 H NMR (400 MHz, CDCl 3 ) δ: 7.32 (d, J = 8.4 Hz, 2H), 6.80 (d, J = 8.4 Hz, 2H), 3.78 (s, 3H), 2.37 (t, J = 7.0 Hz, 2H), (m, 2H), (m, 4H), 0.92 (t, J = 7.0 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 159.0, 132.6, 116.3, 113.8, 88.8, 80.2, 55.2, 31.2, 28.6, 23.5, 19.4, 14.0; LRMS (EI, 70 ev) m/z (%): 202 (M +, 23), 173 (18), 159 (23), 145 (67), 115 (63), 102 (100). 4-(4-Methoxyphenyl)but-3-yn-1-ol (10): 3 1 H NMR (400 MHz, CDCl 3 ) δ: 7.35 (d, J = 8.8 Hz, 2H), 6.83 (d, J = 8.8 Hz, 2H), 3.83 (s, 3H), 3.80 (t, J = 6.4 Hz, 2H), 2.68 (t, J = 6.4 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 159.3, 133.0, 115.4, 113.9, 84.7, 82.3, 61.2, 55.3, 23.9; LRMS (EI, 70 ev) m/z (%): 176 (M +, 33), 158 (-OH, 4), 116 (37), 115 (100). S5
6 3-(4-Methoxyphenyl)prop-2-yn-1-ol (11) 3 1 H NMR (300 MHz, CDCl 3 ) δ: 7.38 (d, J = 8.8 Hz, 2H), 6.84 (d, J = 8.8 Hz, 2H), 4.49 (s, 2H), 3.82 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ: 159.7, 133.2, 114.5, 113.9, 85.8, 85.6, 55.3, 51.7; LRMS (EI, 70 ev) m/z (%): 162 (M +, 21), 144 (-OH, 3), 115 (100). 3-(2-(4-Methoxyphenyl)ethynyl)pyridine (12) 5 1 H NMR (400 MHz, CDCl 3 ) δ: 8.78 (s, 1H), 8.56 (s, 1H0, 7.78 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.8 Hz, 2H), (m, 1H), 6.89 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 160.1, 152.2, 148.2, 138.3, 133.6, 133.2, 114.5, 114.2, 92.8, 84.7, 55.3; LRMS (EI, 70 ev) m/z (%): 209 (M +, 100). 2-(2-Phenylethynyl)benzenamine (13) 3 1 H NMR (400 MHz, CDCl 3 ) δ: (m, 2H), (m, 4H), 7.13 (t, J = 8.8 Hz, 1H), (m, 2H), 4.26 (brs, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 148.6, 132.2, 131.5, 129.8, 128.6, 128.3, 123.4, 118.0, 114.0, 108.0, 94.6, 85.0; LRMS (EI, 70 ev) m/z (%): 193 (M +, 100). 1-(4-(2-Phenylethynyl)phenyl)ethanone (14) 4 1 H NMR (400 MHz, CDCl 3 ) δ: 7.95 (d, J = 8.8 Hz, 2H), 7.61 (d, J = 8.8 Hz, 2H), (m, 2H), 7.38 (t, J = 3.2 Hz, 3H), 2.63 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) S6
7 δ: 197.4, 136.1, 131.8, 131.7, 128.8, 128.4, 128.3, 122.6, 92.7, 88.6, 26.7; LRMS (EI, 70 ev) m/z (%): 220 (M +, 77), 205 (100). 3-(2-Phenylethynyl)pyridine (15) 5 1 H NMR (400 MHz, CDCl 3 ) δ: 8.63 (s, 1H), 7.68 (t, J = 7.6 Hz, 1H), (m, 2H), 7.54 (d, J = 7.6 Hz, 1H), (m, 3H), 7.25 (t, J = 8.0 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ: 150.0, 143.5, 136.2, 132.1, 129.0, 128.4, 127.3, 122.9, 122.3, 89.0, 88.7; LRMS (EI, 70 ev) m/z (%): 179 (M +, 100). 3-(Hept-1-ynyl)pyridine (16) 6 1 H NMR (400 MHz, CDCl 3 ) δ: 8.63 (s, 1H), 8.48 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.21 (t, J = 7.6 Hz, 1H), 2.42 (t, J = 7.2 Hz, 2H), (m, 2H), (m, 4H), 0.93 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 152.4, 147.9, 138.4, 122.9, 121.2, 94.2, 31.1, 28.3, 22.2, 19.4, 14.0; LRMS (EI, 70 ev) m/z (%): 173 (M +, 12), 158 (6), 144 (44), 130 (35), 118 (55), 103 (45), 89 (87), 63 (100). 3-(2-(Pyridin-3-yl)ethynyl)pyridine (18) 5,8 1 H NMR (400 MHz, CDCl 3 ) δ: 8.80 (s, 2H), 8.60 (s, 2H), 7.84 (d, J = 6.8 Hz, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 152.3, 149.1, 138.5, 123.1, 119.8, 89.2; LRMS (EI, 70 ev) m/z (%): 180 (M +, 100). 2-(2-Phenylethynyl)pyrazine (19) 7 S7
8 1 H NMR (400 MHz, CDCl 3 ) δ: 8.77 (s, 1H), 8.59 (s, 1H), 8.49 (s, 1H), 7.63 (d, J = 7.6 Hz, 2H), 7.39 (t, J = 8.4 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 147.8, 144.5, 142.8, 140.4, 132.2, 132.1, 129.6, 128.5, 121.5, 93.3, 85.8; LRMS (EI, 70 ev) m/z (%): 180 (M +, 69), 127 (100). 5-(2-Phenylethynyl)pyrimidine (20) 8 1 H NMR (400 MHz, CDCl 3 ) δ: 9.15 (s, 1H), 8.87 (s, 1H), 7.56 (d, J = 7.6 Hz, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 158.6, 156.6, 131.7, 129.3, 128.5, 121.7, 119.9, 96.3, 82.2; LRMS (EI, 70 ev) m/z (%): 180 (M +, 100). 3-(2-Phenylethynyl)quinoline (21) 8 1 H NMR (400 MHz, CDCl 3 ) δ: 9.02 (s, 1H), 8.34 (s, 1H), 8.12 (d, J = 8.0 Hz, 2H), (m, 2H), (m, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ: 152.2, 146.9, 138.3, 132.1, 131.8, 130.1, 129.5, 128.9, 128.5, 127.6, 127.3, 122.6, 117.5, 92.6, 86.7; LRMS (EI, 70 ev) m/z (%): 229 (M +, 84), 200 (14), 126 (13), 114 (55), 101 (66), 88 (100). 2-(2-Phenylethynyl)thiazole (22) 9 1 H NMR (400 MHz, CDCl 3 ) δ: 7.87 (s, 1H), 7.60 (d, J = 9.6 Hz, 2H), (m, 4H); 13 C NMR (100 MHz, CDCl 3 ) δ: 154.6, 143.6, 131.9, 129.5, 128.5, 121.4, 120.8, 93.9, 82.2; LRMS (EI, 70 ev) m/z (%): 185 (M +, 100) S8
9 2-(2-Phenylethynyl)pyrimidine (24) 8 1 H NMR (400 MHz, CDCl 3 ) δ: 8.77 (s, 1H), 7.68 (d, J = 7.6 Hz, 2H), 7.40 (t, J = 8.0 Hz, 3H), 7.26 (t, J = 5.2 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ: 157.3, 153.4, 132.6, 129.7, 128.7, 121.3, 119.7, 88.1, 87.9; LRMS (EI, 70 ev) m/z (%): 180 (M +, 100) (B) References (1) (a) Xu, H.; Wang, W.; Zhu, W. J. Phys. Chem. B. 2006, 110, (b) C. H. B. Ng, W. Y. Fan, J. Phys. Chem. B. 2006, 110, (c) Guo, L.; Murphy, C. J.; Nano Lett. 2003, 3, 231. (d) Zhang, J.; Liu, J.; Peng, Q.; Wang, X.; Li, Y. Chem. Mater. 2006, 18, 867. (e) Wu, W.-T.; Wang, Y.; Shi, L.; Pang, W.; Zhu, Q.; Xu, G.; Lu, F. J. Phys. Chem. B. 2006, 110, (f) Yao, W.-T.; Yu, S.-H.; Zhou, Y.; Jiang, J.; Wu, Q.-S.; Zhang, L.; Jiang, J. J. Phys. Chem. B. 2005, 109, (2) (a) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, (c) Ma, D, Liu, F. Chem. Commun. 2004, (d) Saejueng, P.; Bates, C. G.; Venkataraman, D. Synthesis. 2005, (e) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, (f) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, (g) Méry, D.; Heuzé, K.; Astrc, D. Chem. Commun. 2003, (h) Gelman, D.; Buthwald, S. L. Angew. Chem. Int. Ed. 2003, 42, (i) Wolf, C.; Lerebours, R. Org. Biomol. Chem. 2004, 2, (j) Heuzé, K.; Méry, D.; Gauss, D.; Blais, J.-C.; Astruc, D. Chem. Eur. J. 2004, 10, S9
10 (3) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synthesis 2004, (4) Liu, L.; Zhang, Y.; Xin, B. J. Org. Chem. 2006, 71, (5) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2005, 46, (6) Wang, B.; Bonin, M.; Micouin, L. Org. Lett. 2004, 6, (7) Beccalli, E. M.; Manfredi, A.; Marchesini, A. J. Org. Chem. 1985, 50, (8) Sorensen, U. S.; Pombo-Villar, E. Tetrahedron 2005, 61, (9) Karpov, A. S.; Rominger, F.; Mueller, T. J. J. J. Org. Chem. 2003, 68, 1503 S10
11 (C) Spectra Fig. 1 TEM picture showing octahedral Cu 2 O nanoparticles. % Nanoparticles diameter (nm) Fig. 2 Histogram of the Cu 2 O nanoparticles size distribution and XRD pattern of the octahedral Cu 2 O nanoparticles. S11
12 Fig. 3 TEM picture showing spherical Cu 2 O nanoparticles. Fig. 4 XRD pattern of the spherical Cu 2 O nanoparticles. S12
13 1-(2-(4-nitrophenyl)ethynyl)benzene (3) S13
14 1-(2-(4-nitrophenyl)ethynyl)benzene (3) S14
15 1,2-diphenylethyn (4) S15
16 1,2-diphenylethyn (4) S16
17 1-(Hept-1-ynyl)benzene (5) S17
18 1-(Hept-1-ynyl)benzene (5) S18
19 4-Phenylbut-3-yn-1-ol (6) S19
20 4-Phenylbut-3-yn-1-ol (6) S20
21 1-(2-o-tolylethynyl)benzene (7) S21
22 1-(2-o-tolylethynyl)benzene (7) S22
23 1-Methoxy-4-(2-phenylethynyl)benzene (8) S23
24 1-methoxy-4-(2-phenylethynyl)benzene (8) S24
25 1-(Hept-1-ynyl)-4-methoxybenzene (9) S25
26 1-(Hept-1-ynyl)-4-methoxybenzene (9) S26
27 4-(4-Methoxyphenyl)but-3-yn-1-ol (10) S27
28 4-(4-Methoxyphenyl)but-3-yn-1-ol (10) S28
29 3-(4-Methoxyphenyl)prop-2-yn-1-ol (11) S29
30 3-(4-Methoxyphenyl)prop-2-yn-1-ol (11) S30
31 3-(2-(4-Methoxyphenyl)ethynyl)pyridine (12) S31
32 3-(2-(4-Methoxyphenyl)ethynyl)pyridine (12) S32
33 2-(2-Phenylethynyl)benzenamine (13) S33
34 2-(2-Phenylethynyl)benzenamine (13) S34
35 1-(4-(2-Phenylethynyl)phenyl)ethanone (14) S35
36 1-(4-(2-Phenylethynyl)phenyl)ethanone (14) S36
37 3-(2-Phenylethynyl)pyridine (15) S37
38 3-(2-Phenylethynyl)pyridine (15) S38
39 3-(Hept-1-ynyl)pyridine (16) S39
40 3-(Hept-1-ynyl)pyridine (16) S40
41 3-(2-(Pyridin-3-yl)ethynyl)pyridine (18) S41
42 3-(2-(Pyridin-3-yl)ethynyl)pyridine (18) S42
43 2-(2-Phenylethynyl)pyrazine (19) S43
44 2-(2-Phenylethynyl)pyrazine (19) S44
45 5-(2-Phenylethynyl)pyrimidine (20) S45
46 5-(2-Phenylethynyl)pyrimidine (20) S46
47 3-(2-Phenylethynyl)quinoline (21) S47
48 3-(2-Phenylethynyl)quinoline (21) S48
49 2-(2-Phenylethynyl)thiazole (22) S49
50 2-(2-Phenylethynyl)thiazole (22) S50
51 2-(2-Phenylethynyl)pyrimidine (24) S51
52 2-(2-Phenylethynyl)pyrimidine (24) S52
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