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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting information Ag-doped ano Magnetic γ-fe 2 O Core Shell Hollow Spheres: an efficient and recoverable heterogeneous catalyst for A 3, KA 2 Coupling Reactions and [2+3] cycloaddition A. Elhampour *,a, M. Malmir *,b E. Kowsari, F. Boorboor ajdari and F. emati a Department of Chemistry, Semnan University, Semnan, Iran, Zip Code: , Elhampour_ali@yahoo.com b Department of Chemistry, Amirkabir University of Technology, Hafez Avenue, o. 424, Tehran, Iran, address: Masi.malmir@yahoo.com 1
2 1. General information S General details S3 2. Characterizations of Catalyst S FT-IR analysis S XRD patterns S TGA analysis S VSM Curves S FEG-SEM-EDS analysis S TEM image S7 3. Spectral data for selected compounds S8-S Copies of 1 H and 13 C MR for selected products S16-S55 4. Reference S56 2
3 1. General information The process for the preparation of the magnetic Fe 2 O hollow sphere catalyst is schematically described in scheme 1. The nano magnetic Fe 2 O hollow sphere was prepared from commercially inexpensive available materials and fully characterized using, the corresponding data, provided by FT-IR, FE-SEM, TEM, XRD, TGA, and VSM techniques General details All chemicals, including FeCl 3 6H 2 O, trisodium citrate dihydrate, sodium acetate trihydrate, ethanol, ethylene glycol (EG), PVP, urea, dopamine, AgO 3 and H 3 H 2 O, were analytical grade reagents, purchased from Sigma-Aldrich, and used without further purification. The progress of reaction was monitored by TLC on commercial aluminumbacked plates of silica gel 60 F254, visualized, using ultraviolet light. Melting points were determined in open capillaries using an Electrothermal 9100 without further corrections. 1 H MR and 13 C MR spectra were recorded using a Bruker DRX-400 spectrometer at 400 and 100 MHz respectively. magnetic-fe 2 O hollow sphere was characterized by; FT-IR spectra were obtained with potassium bromide pellets in the range of cm -1 using a Shimadzu 8400s spectrometer; X-ray diffraction (XRD) was detected by Philips using Cu-Ka radiation of wavelength 1.54Å; Scanning electron Microscopy, FE-SEM-EDX, analysis was performed using Tescanvega II XMU Digital Scanning Microscope. Samples were coated with gold at 10 ma for 2 min prior to analysis; the magnetic properties were characterized using a vibrating sample magnetometer (VSM, Lakeshore7407) at room temperature. Thermo-gravimetric 3
4 analyses (TGA) were analyzed with a LISEIS modele STS PT thermal analyzer under air atmosphere at a heating rate of 5 C min Characterizations of Catalyst 2.1. FT-IR analysis Figure 1. The FT-IR spectra of (a) h-fe 2 O 3, (b) h-fe 2 O and (c) h-fe 2 O 4
5 2.2. X-ray diffraction spectra Figure 2. XRD pattern of (a) h-fe 2 O 3, (b) h-fe 2 O and (c) h-fe 2 O 2.3. X-ray diffraction spectra Figure 3. TGA analysis of (a) h-fe 2 O 3 and (b) h-fe 2 O 5
6 2.4. VSM analysis Figure 4. The magnetization curves of (a) h-fe 2 O 3, (b) h-fe 2 O and (c) h-fe 2 O 2.5. FE-SEM-EDS analysis (a) (c) (e) (b) (d) (f) Figure 5. The FEG-SEM-EDS analysis of (a,b) h-fe 2 O 3, (c,d) h-fe 2 O and (e,f) h- Fe 2 O 6
7 2.6. TEM image Ag nanoparticles Figure 6. The TEM image of h-fe 2 O 7
8 3. Spectral data for selected compounds 1-(1,3-diphenylprop-2-ynyl)piperidine (table 1, 5a): Pale yellow oily liquid; 1 H MR (400 MHz, CDCl 3, ppm) δ (m, 2H), (m, 4H), 2.59 (t, 4H), 4.81 (s, 1H), (m, 6H), (m, 2H), (d, J=7.6 Hz, 2H). S 1-(3-phenyl-1-(thiophen-2-yl)prop-2-ynyl)piperidine (table 1, 5g): Yellow solid; mp o C (Lit o C); 1 H MR (400 MHz, CDCl 3, ppm) δ (m, 2H), (m, 4H), (m, 4H), 5.03 (s, 1H), 7.00 (dd, J 1 =J 2 =3.6 Hz, 1H), (m, 1H), 7.31 (d, J=4.4 Hz, 2H) (m, 3H), (m, 2H); 13 C MR (100 MHz, CDCl 3, ppm) δ 24.4, 26.1, 50.6, 58.2, 85.3, 86.9, 123, 125.3, 125.8, 126.2, 128.2, 128.3, 131.8,
9 1-(3-phenyl-1-(4-(3-phenyl-1-(piperidin-1-yl)prop-2-ynyl)phenyl)prop-2- ynyl)piperidine (table 1, 5h): White solid; mp o C (Lit o C); 1 H MR (400 MHz, CDCl 3, ppm) δ 1.47 (m, 2H), (m, 4H), 2.59 (m, 4H), 4.81 (s, 1H), (m, 3H), (m, 2H), 7.63 (s, 2H). 1-(1-(naphthalen-3-yl)-3-phenylprop-2-ynyl)piperidine (table 1, 5i): Yellow oil; 1 H MR (400 MHz, CDCl 3, ppm): δ (m, 2H), (m, 4H), 2.64 (t, 4H), 4.97 (s, 1H), (m, 3H), (m, 2H), (m, 2H), 7.79 (dd, J 1 =J 2 =8.4 Hz, 1H), (m, 3H), 8.11 (s, 1H); 13 C MR (100 MHz, CDCl 3, ppm) d 24.4, 26.2, 50.8, 62.5, 86, 88.1, 123.3, 125.8, 125.9, 126.7, 127.2, 127.5, 127.7, 128.1, , 131.8, 132.9, 133.1,
10 ,-diethyl-1,3-diphenylprop-2-yn-1-amine (table 1, 5r): Pale yellow oily liquid; 1 H MR (400 MHz, CDCl 3, ppm) δ 1.04 (m, 6H), (m, 4H), 5.19 (s, 1H), (m, 4H), (m, 3H), (m, 2H). O 4-(3-phenylprop-2-ynyl)morpholine (table 1, 6c): yellow oil; 1 H MR (400 MHz, CDCl 3, ppm) δ ,67 (m, 6H), 3.52 (s, 3H), (m, 1H), (m, 6H), (m, 4H), (m, 2H). 1-(1-cyclohexyl-3-phenylprop-2-ynyl)pyrrolidine (table 1, 6i): Colorless liquid; 1 H MR (400 MHz, CDCl 3, ppm) δ (m, 5H), (m, 2H), (m, 6H), (m, 4H), (m, 4H), (d, J =7.6 Hz, 1H), (m, 10
11 3H), (m, 2H). 13 C MR (100 MHz, CDCl 3, ppm) δ 24.9, 26.9, 27.1, 28.3, 32.7, 33, 42.9, 51.1, 61.1, 86.1, 88.9, 125.9, 128.9, 129.8, O 4-(1-phenylhex-1-yn-3-yl)morpholine (Table 1, 6m): Yellow oil; 1 H MR (400 MHz, DMSO-d 6, ppm) δ 0.97 (m, 3H), (m, 4H), (m, 2H), (m, 2H), (m, 1H), (m, 4H), (m, 3H), (m, 2H). 1-(1-(2-p-tolylethynyl)cyclohexyl)piperidine (Table 2, 8e): Yellow oil; 1 H MR (400 MHz, CDCl 3, ppm) δ (m, 16H), (m, 2H), 2.53 (s, 3H), (m, 2H), (m, 3H), (m, 2H); 13 C MR (100 MHz, CDCl 3, ppm) δ 21.32, 23.4, 24.4, 25, 26.7, 37.6, 47.9, 58.8, 85.4, 92.1, 123, 127.6, 128.3, 133. O 11
12 4-(1-(2-phenylethynyl)cyclohexyl)morpholine (Table 2, 8f): Pale yellow oily liquid; 1 H MR (400 MHz, CDCl 3, ppm) δ (m, 1H), 1.52 (m, 2H), (m, 3H), 1.73 (br.s, 2H), (m, 2H), 2.74 (br.s, 4H), 3.78 (br.s, 4H), 7.27 (m, 3H), (m, 2H), 13 C MR (100 MHz, CDCl 3, ppm) δ 22.7, 25.7, 35.4, 46.6, 58.8, 67.4, 86.4, 89.8, 123.4, 127.7, 128.1, O F 4-(1-( (4-fluorophenyl)ethynyl)cyclohexyl)morpholine (Table 2, 8i): Yellow oil; 1 H MR (400 MHz, DMSO-d 6, ppm) δ (m, 1H), (m, 2H), (m, 3H), (m, 2H), (m, 2H), 2.78 (s, 4H), 3.70 (br.t, J = 4.2 Hz, 4H), (t, J = 8.6 Hz, 2H), (m, 2H). H 5-Phenyl-1H-tetrazole (Table 3, 9a): White solid; mp o C (Lit o C); 1 H MR (400 MHz, DMSO-d 6, ppm) δ 7.68 (s, 3H, Ph), 7.92 (s, 2H, Ph); 13 C MR (100 MHz, DMSO-d 6, ppm) δ 126.6, 128.6, 130.3, 134.6, 155. H O 2 12
13 5-(4-itrophenyl)-1H-tetrazole (Table 3, 9b): Yellow solid; mp o C (Lit o C); 1 H MR (400 MHz, DMSO-d 6, ppm) δ 8.30 (d, 2H, J 8.4, Ph), 8.39 (d, 2H, J 8.8, Ar-H); 13 C MR (100 MHz, DMSO-d 6, ppm) δ 127.6, 129.1, 131, H 5-(4-Methylphenyl)-1H-tetrazole (Table 3, 9c): White solid; mp o C (Lit o C); 1 H MR (250 MHz, DMSO-d 6, ppm) δ 2.35 (s, 3H, CH 3 ), 7.37 (d, 2H, J 7.6 Hz, Ph), 7.90 (d, 2H, J 7.5 Hz, Ph). Cl H 5-(3-Chlorophenyl)-1H-tetrazole (Table 3, 9g): White solid; mp o C (Lit o C); 1 H MR (250 MHz, DMSO-d 6, ppm) δ 7.55 (m, 2H, Ph), 7.96 (d, 1H, J 7.6, Ph), 7.99, (s, 1H); 13 C MR (62.9 MHz, DMSO-d 6, ppm) δ 125.4, 126.2, 126.4, 130.7, 131.1, 133.9, H Cl 5-(4-Chlorophenyl)-1H-tetrazole (Table 3, 9h): White solid; mp o C (Lit o C); 1 H MR (400 MHz, DMSO-d 6, ppm) δ 7.61 (d, 2H, J 8.4, Ph), 8.09 (d, 2H, J 8.8, Ph). 13
14 H HO 5-(4-Hydroxyphenyl)-1H-tetrazole (Table 3, 9j): White solid; mp 235 o C (Lit o C); 1 H MR (400 MHz, DMSO-d 6, ppm) δ 6.91 (d, 2H, J 8.4, Ph), 7.58 (d, 2H, J 8.4, Ph), (s broad, OH); 13 C MR (100 MHz, DMSO-d 6, ppm) δ 116.1, 117.4, 128.8, 153.2, H C 4-(1H-tetrazol-5-yl)-benzonitrile (Table 3, 9k): White solid; mp o C (Lit o C); 1 H MR (250 MHz, DMSO-d 6, ppm) δ 8.06 (d, 2H, J 7.1, Ph), 8.19 (d, 2H, J 8.6, Ar-H); 13 C MR (62.9 MHz, DMSO-d 6, ppm) δ 113.3, 118.1, 127.6, 128.7, 133.1, 155.2, H 2-(1H-tetrazol-5-yl)pyridine (Table 3, 9l): White solid; mp o C (Lit o C); 1 H MR (400 MHz, DMSO-d 6, ppm) δ 7.75 (s, 1H, Ph), 8.07 (s, 1H, Ph), 8.20 (d, 1H, J 8.4 Ph), 8.63 (s, 1H). 14
15 H 4-(1H-tetrazol-5-yl)pyridine (Table 3, 9m): White solid; mp o C (Lit o C); 1 H MR (250 MHz, DMSO-d 6, ppm) δ 8.10 (d, 2H, J 6.0, Ph), 8.77 (d, 2H, J 6.5, Ph); 13 C MR (62.9 MHz, DMSO-d 6, ppm) δ 120.9, 121.3, 133.8, 149.9,
16 3.1. Copies of 1H and 13C MR for selected products Figure 7. 1 H MR spectrum of (table 1, 5a) 16
17 Figure 8. 1 H MR, Expand spectrum of (table 1, 5a) 17
18 Figure 9. 1 H MR, spectrum of (table 1, 5g) 18
19 Figure 10 1 H MR, Expand spectrum of (table 1, 5g) 19
20 Figure C MR, Expand spectrum of (table 1, 5g) 20
21 Figure C MR, Expand spectrum of (table 1, 5g) 21
22 Figure 13 1 H MR, spectrum of (table 1, 5h) 22
23 Figure 14 1 H MR, Expand spectrum of (table 1, 5h) 23
24 Figure 15 1 H MR, spectrum of (table 1, 5i) 24
25 Figure 16 1 H MR, Expand spectrum of (table 1, 5i) 25
26 Figure C MR, spectrum of (table 1, 5i) 26
27 Figure C MR, Expand spectrum of (table 1, 5i) 27
28 Figure 19 1 H MR, spectrum of (table 1, 5r) 28
29 Figure 20 1 H MR, spectrum of (table 1, 6c) 29
30 Figure 21 1 H MR, Expand spectrum of (table 1, 6c) 30
31 Figure 22 1 H MR, spectrum of (table 1, 6i) 31
32 Figure C MR, spectrum of (table 1, 6i) 32
33 Figure 24 1 H MR, spectrum of (table 1, 6m) 33
34 Figure 25 1 H MR, spectrum of (table 2, 8e) 34
35 Figure 26 1 H MR, Expand spectrum of (table 2, 8e) 35
36 Figure C MR, spectrum of (table 2, 8e) 36
37 Figure 28 1 H MR, spectrum of (table 2, 8f) 37
38 Figure C MR, spectrum of (table 2, 8f) 38
39 Figure 30 1 H MR spectrum of (table 2, 8i) 39
40 Figure 31 1 H MR spectrum of (table 3, 9a) 40
41 Figure C MR spectrum of (table 3, 9a) 41
42 Figure 33 1 H MR spectrum of compound (table 3, 9b) 42
43 Figure C MR spectrum of (table 3, 9b) 43
44 Figure 35 1 H MR spectrum of (table 3, 9c) 44
45 Figure C MR spectrum of (table 3, 9c) 45
46 Figure 37 1 H MR spectrum of (table 3, 9g) 46
47 Figure 38 1 H MR spectrum of (table 3, 9h) 47
48 Figure 39 1 H MR spectrum of (table 3, 9j) 48
49 Figure C MR spectrum of (table 3, 9j) 49
50 Figure 41 1 H MR spectrum of (table 3, 9k) 50
51 Figure 42 1 H MR expand spectrum of (table 3, 9k) 51
52 Figure C MR spectrum of (table 3, 9k) 52
53 Figure 44 1 H MR spectrum of (table 3, 9l) 53
54 Figure 45 1 H MR spectrum of (table 3, 9m) 54
55 Figure C MR spectrum of (table 3, 9m) 55
56 4. References 1. M. Tajbakhsh, M. Farhang, M. Baghbanian, R. Hosseinzadeh and M. Tajbakhsh, ew J. Chem., 2015, 39, G. A. Meshrama, S. S. Deshpandea, P. A. Wagha and V. A. Vala, Tetrahedron Lett., 2014, 4, A. Khalafi-ezhad and S. Mohammadi, RSC Adv., 2013, 3, A. I. Azath, P. Suresh and K. Pitchumani, ew J. Chem., 2012, 36, V. Rama, K. Kanagaraj and K. Pitchumani J. Org. Chem., 2011, 76, M. Esmaeilpour, J. Javidi, F. owroozi Dodeji and M. Mokhtari Abarghoui, J. Mol. Catal. A: chem., 2014, 393,
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