Supporting Information for. Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron. Reagents to C-C Double Bonds.
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- ÏἈχαϊκός Κοτζιάς
- 5 χρόνια πριν
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1 Supporting Information for Impregnated Copper on Magnetite as Recyclable Catalyst for the Addition of Alkoxy Diboron Reagents to C-C Double Bonds. Rafael Cano, Diego J. Ramón* and Miguel Yus Instituto de Síntesis rgánica (IS) and Departamento de Química rgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E Alicante, Spain Table of Contents General information. General Procedure for the preparation of impregnated copper catalyst General procedure for the catalyzed borylation process Spectra data for products Spectra data for products 5 References..... Copies of 1 H and 13 C-NMR S2 S2 S2 S3 S5 S6 S8 S1
2 General Information: Melting points were obtained with a Reichert Thermovar apparatus. NMR spectra were recorded on a Bruker AC-300 (300 MHz for 1 H and 75 MHz or 13 C) using CDCl3 as a solvent and TMS as internal standard; chemical shifts are given in δ (parts per million) and coupling constants (J ) in Hertz. FT-IR spectra were obtained on a Nicolet Impact 400D spectrophotometer. Mass spectra (EI) were obtained at 70 ev on a Himazdu QP-5000 spectrometer, giving fragment ions in m/z with relative intensities (%) in parentheses. Thin layer chromatography (TLC) was carried out on Schleicher & Schuell F1400/LS 254 plates coated with a 0.2 mm layer of silica gel; detection by UV254 light, staining with phosphomolybdic acid [25 g phosphomolybdic acid, 10 g Ce(S4 )2 4H2, 60 ml of concentrated H2 S4 and 940 ml H2 ]. Column chromatography was performed using silica gel 60 of mesh. All reagents were commercially available (Acros, Aldrich, Fluorochem) and were used as received. Surface areas were determined by the application of the BET equation to the N 2 adsorption isotherm at 77K. Adsorption data were obtained with a QUANTACHRME AUTSRB-6 equipment. FAAS analyses were carried out using a Varian SpectrAA 10 plus Atomic Absorption Spectrometer. X-ray fluorescence data were obtained with a PHILIPS MAGIX PR equipment. General procedure for the preparation of impregnated copper catalyst: To a stirred solution of CuCl 2 (0.13 g, 1 mmol) in deionised water (120 ml) was added Fe 3 4 (4 g, 17 mmol, powder < 5 μm, BET area: 9.86 m 2 g -1 ). After 10 min at room temperature, the mixture was slowly basified with NaH 1 M until ph around 13. The resulting basified mixture was stirred during approximately 24 h and then filtrated under vacuum. The solid catalyst was washed several times with deionised water (3 x 50 ml) and dried during three days at room temperature (BET area: 9.15 m 2 g -1 ). Incorporation of % of Cu according to X-ray fluorescence. General procedure for the catalyzed borylation process: To a stirred solution of bis(pinacolato)diboron (1, 0.7 mmol, 178 mg) in toluene (0.5 ml) under argon atmosphere were added Cu(H) x /Fe 3 4 (50 mg), K 2 C 3 (0.45 mmol, 62 mg), the α,β-unsaturated compound or olefin (2 or mmol) and MeH (1 mmol, 40 μl). The resulting mixture was stirred at S2
3 60ºC until end of reaction. The catalyst was removed by a magnet and the resulting mixture was quenched with a saturated solution of NH 4 Cl and extracted with AcEt. The organic phases were dried over MgS 4, followed by evaporation under reduced pressure to remove the solvent. The product was usually purified by chromatography on silica gel (hexane/ethyl acetate). Spectra data of products 3 B NH 2 3-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide 1 (3ª): Mp ºC; R f = 0.29 (EtAc); IR (KBr): ν 3372, 3178, 2971, 1662, 1308, 1241, 1128, 700 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.18 (s, 6H), 1.21 (s, 6H), (m, 1H), (m, 1H), (m, 1H), 5.42 (s, 2H), ppm (m, 5H); 13 C NMR (400 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.5, 24.5, 38.9, 83.5, 125.6, 125.7, 128.5, 141.6, ppm; EI-MS m/z: 276 (M + +1, 17%), 275 (M +, 100), 274 (40), 260 (16), 218 (34), 217 (47), 216 (29), 176 (49), 175 (78), 174 (82), 173 (18), 132 (51), 131 (55), 130 (38), 129 (11), 117 (31), 116 (14), 115 (18), 105 (45), 104 (75), 103 (30), 99 (24), 98 (30), 91 (25), 83 (33), 78 (20), 77 (24), 69 (11), 59 (18), 57 (12), 55 (24). B NH 2 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide (3b): Mp ºC; R f = 0.7 (Hexane/EtAc 4:1); IR (KBr): ν 3418, 1676, 1549, 1315, 1115 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.05 (t, J = 7.5 Hz, 2H), 1.25 (s, 12H), 2.37 ppm (t, J = 7.4 Hz, 2H), , (2 br s, 1 and 1H, respectively); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ = 24.8, 30.2, 83.3, ppm; EI-MS m/z: 184 (10), 141 (94), 140 (100), 139 (197), 100 (25), 99 (15), 84 (20), 83 (16), 55 (10). Anal. Calcd (%) for C 9 H 18 BN 3 : C, 54.30; H, 9.11; N, Found C, 54,32; H, 9.09; N, B Et Ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propionate 2 (3c): R f = 0.27 (Hexane/EtAc 4:1); IR (film): ν 1729, 1449, 1375, 1120 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (m, 15H), (m, 2H), (m, 1H), 4.1 (q, J = 4Hz, 2H), ppm (m, 5H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 14.2, 24.5, 24.6, 37.3, 60.3, 83.5, 125.6, 128.2, 128.4, 141.3, ppm; EI-MS m/z: 304 (M +, 45%), 303 (12), 259 (15), 246 (22), 233 (63), 232 (16), 176 (16), 175 (12), 145 (15), 132 (23), 131 (46), 129 (12), 117 (24), 105 (36), 104 (100), 103 (19), 91 (10), 83 (61), 78 (11), 77 (11), 55 (14). S3
4 3-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propionitrile 3 (3d): R f = B CN 0.37 (Hexane/EtAc 4:1); IR (film): ν 2243, 1362, 1328, 1128 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.22 (s, 6H), 1.25 (s, 6H), (m, 3H), ppm (m, 5H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 20.6, 24.4, 24.6, 84.3, 119.5, 126.6, 128.1, 128.8, ppm; EI-MS m/z: 257 (M +, 26%), 256 (12), 242 (12), 217 (19), 117 (35), 105 (12), 104 (100), 85 (14), 83 (12). 4-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-2-one 4 (3e): R f = B 0.37 (Hexane/EtAc 4:1); IR (film): ν 1709, 1369, 1315, 1135 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.16 (s, 6H), 1.21 (s, 6H), 2.12 (s, 3H), (m, 1H), (m, 1H), (m, 1H), ppm (m, 5H); 13 C NMR (400 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.4, 29.5, 47.4, 83.3, 125.4, 128.1, 128.4, 141.6, ppm; EI-MS m/z: 274 (M +, 0.2%), 259 (51), 258 (12), 216 (29), 191 (63), 190 (17), 174 (71), 173 (31), 159 (40), 158 (18), 157 (13), 147 (42), 145 (47), 144 (13), 143 (11), 133 (11), 132 (65), 131 (82), 130 (100), 129 (85), 128 (26), 127 (14), 125 (12), 118 (54), 117 (48), 116 (28), 115 (84), 105 (23), 104 (21), 103 (19), 101 (15), 91 (45), 85 (10), 84 (60), 83 (27), 78 (13), 77 (19), 69 (17), 59 (14), 55 (23). 1,3-Diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-one 5 B (3f): Mp ºC; R f = 0.6 (Hexane/EtAc 4:1); IR (KBr): ν 1676, 1362, 1308, 1135 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.17 (s, 6H), 1.25 (s, 6H), (m, 1H), (m, 1H), (m, 1H), ppm (m, 10H); 13 C NMR (400 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.5, 24.5, 43.2, 83.3, 125.6, 128, 128.3, 128.4, 128.5, 132.9, 136.7, 141.9, ppm; EI-MS m/z: 336 (M +, 6%), 321 (12), 278 (28), 254 (12), 253 (77), 252 (23), 237 (17), 236 (100), 235 (46), 210 (11), 209 (68), 193 (24), 192 (67), 191 (54), 189 (11), 178 (13), 159 (12), 132 (16), 131 (18), 117 (15), 116 (11), 115 (34), 105 (68), 104 (20), 103 (62), 90 (17), 84 (32), 83 (12), 78 (10), 77 (63), 69 (11), 55 (15), 51 (11). 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetrahidropyran-2-one 6 (3g): R f = 0.53 (Hexane/EtAc 4:1); IR (film): ν 1722, 1449, 1375, 1321, 1148 cm -1 ; 1 H NMR B (300 MHz, CDCl 3 ): δ 1.25 (s, 12H), (m, 3H), (m, 2H), ppm (m, 2H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 23.9, 24.5, 24.7, 30.9, 69.9, 83.9, ppm; EI-MS m/z: 226 (M +, 2%), 211 (9), 183 (22), 168 (49), 167 (15), 153 (23), 141 (11), 140 (100), 139 (47), 127 (23), 126 (17), 125 (30), 99 (12), 98 (10), 97 (13), S4
5 96 (23), 85 (25), 84 (18), 83 (29), 82 (18), 81 (23), 69 (15), 68 (13), 59 (16), 57 (11), 56 (11), 55 (41), 54 (12). 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexanone 6 (3h): R f = 0.43 B (Hexane/EtAc 4:1); IR (KBr): ν 1709, 1375, 1322, 1135 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.24 (s, 12H), (m, 1H), (m, 2H), (m, 1H), (m, 1H), ppm (m, 4H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.4, 24.5, 26.2, 28.2, 41.6, 42.3, 83.2, ppm; EI-MS m/z: 225 (M + +1, 10%), 224 (M +, 74), 223 (18), 209 (38), 196 (25), 181 (37), 167 (31), 166 (100), 165 (28), 154 (11), 153 (55), 152 (29), 151 (23), 140 (21), 139 (32), 138 (43), 137 (20), 129 (57), 128 (15), 125 (20), 124 (34), 123 (32), 122 (23), 113 (10), 111 (25), 110 (80), 109 (18), 108 (24), 107 (57), 101 (27), 97 (33), 96 (41), 95 (31), 94 (15), 93 (21), 85 (56), 84 (58), 83 (93), 82 (23), 81 (86), 80 (56), 79 (48), 69 (53), 68 (33), 67 (49), 66 (14), 59 (58),58 (10), 57 (42), 56 (11), 55 (92), 54 (18), 53 (31). Spectra data of products 5 B 2-(2-phenylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 7 (5a): R f = 0.67 (Hexane/EtAc 4:1); IR (film): ν 1366, 1312, 1140, 962, 843 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.15 (t, J = 8.2 Hz, 2H), 1.22 (s, 12H), 2.75 (t, J = 8.1 Hz, 2H), ppm (m, 5H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.8, 29.9, 83.1, 125.5, 128, 128.1, ppm; EI-MS m/z: 232 (M +, 16%), 217 (18), 175 (56), 174 (18), 146 (12), 133 (17), 132 (73), 131 (41), 105 (51), 104 (18), 91 (88), 85 (19), 84 (100), 78 (10), 77 (12), 69 (13), 65 (11), 59 (14). B 2-(2-(2-Naphthyl)ethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 7 (5b): Mp ºC; R f = 0.67 (Hexane/EtAc 4:1); IR (KBr): ν 1362, 1302, 1121, 848, 807 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.19 (s, 12H), (m, 2H), 2.91 (t, J = 8.1 Hz, 2H), (m, 3H), 7.63 (s, 1H), ppm (m, 3H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.7, 30, 83, 124.8, 125.6, 125.6, 127.2, 127.3, 127.5, 127.6, 131.8, 133.6, ppm; EI-MS m/z: 283 (M + +1, 13%), 282 (M +, 66), 281 (16), 225 (17), 182 (36), 181 (28), 166 (34), 165 (12), 164 (18), 163 (10), 155 (36), 154 (100), 153 (13), 141 (69), 115 (17), 84 (45). S5
6 Cl B 2-(2-(4-Chlorophenyl)ethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 8 (5c): R f = 0.7 (Hexane/EtAc 4:1); IR (film): ν 1384, 1318, 1128, 1087, 968, 849 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.14 (t, J = 9.5 Hz, 2H), 1.21 (s, 12H), 2.71 (t, J = 8.1 Hz, 2H), ppm (2d, J = 8.4 Hz, 2H and 2H, respectively); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.8, 29.3, 83.2, 128.2, 129.4, 131.1, ppm; EI-MS m/z: 266 (M +, 14%), 251 (14), 211 (14), 209 (42), 208 (13), 167 (10), 166 (18), 165 (16), 150 (12), 139 (18), 131 (32), 127 (18), 125 (52), 85 (15), 84 (100), 59 (14). B 2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 9 (5d): R f = 0.63 (Hexane/EtAc 4:1); IR (film): ν 1360, 1306, 1140, 968, 849 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (m with s at 1.15, 14H), 1.27 (d, J = 7 Hz, 3H), (m, 1H), (m, 5H) ppm; 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 24.6, 24.7, 24.8, 35.8, 82.9, 125.6, 126.6, 128.1, ppm; EI-MS m/z: 246 (M +, 21%), 231 (49), 230 (16), 202 (11), 146 (35), 145 (23), 131 (26), 130 (13), 128 (15), 118 (13), 105 (100), 104 (17), 103 (13), 85 (10), 84 (91). 2-hexyl-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 10 (5e): R f = 0.40 B (Hexane/EtAc 4:1); IR (film): ν 1306, 1135 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (m, 2H), (m, 3H), (m, 18H), ppm (m, 2H); 13 C NMR (300 MHz, CDCl 3, C attached to quadrupole B not observed): δ 14.1, 15.5, 22.9, 24.7, 31.2, 32.9, 82.7 ppm; EI-MS m/z: 212 (M +, 3%), 198 (12), 197 (100), 196 (25), 170 (11), 154 (12), 141 (10), 129 (46), 128 (17), 127 (13), 126 (65), 113 (26), 112 (57), 111 (25), 101 (24), 97 (11), 87 (16), 85 (63), 84 (79), 83 (59), 71 (65), 70 (21), 69 (30), 59 (22), 57 (24), 56 (12), 55 (28). References (1) Chea, H.; Sim, H.-S.; Yun, J. Adv. Synth. Catal. 2009, 351, (2) Shiomi, T.; Adachi, T.; Toribatake, K.; Zhou, L.; Nishiyama, H. Chem. Commun.2009, (3) Mun, S.; Lee, J.-E.; Yun, J. rg. Lett. 2006, 8, 21, (4) Gao, M.; Thorpe, S. B.; Santos, W. L. rg. Lett. 2009, 11, 15, (5) Bell, N. J.; Cox, A. J.; Cameron, N. R.; Evans, J. S..; Marder, T. B.; Duin, M. A.; Elsevier, C. S6
7 J.; Baucherel, X.; Tulloch, A. A. D.; Tooze, R. P. Chem. Commun. 2004, (6) Feng, X.; Yun, J. Chem. Commun. 2009, (7) Yamamoto, Y.; Fujikawa, R.; Umemoto, T.; Miyaura, N. Tetrahedron, 2004, 60, (8) Crudden, C. M.; Hleba, Y. B.; Chen, A. C. J. Am. Chem. Soc, 2004, 126, (9) Karatjas, A. G.; Vedejs, E. J. rg. Chem, 2008, 73, (10) Caballero, A.; Sabo-Ettienne, S. rganometallics, 2007, 26, S7
8 S8
9 13 C NMR (400MHz, CDCl 3 ) S9
10 1 H NMR (300 MHz, CDCl 3 ) S10
11 13 C NMR (300 MHz, CDCl 3) S11
12 1 H NMR (300 MHz, CDCl 3 ) S12
13 13 C NMR (300 MHz, CDCl 3) S13
14 S14
15 13 C NMR (300 MHz, CDCl 3) S15
16 1 H NMR (400 MHz, CDCl 3 ) S16
17 13 C NMR (400 MHz, CDCl 3) S17
18 1 H NMR (300 MHz, CDCl 3 ) S18
19 13 C NMR (400 MHz, CDCl 3) S19
20 1 H NMR (300 MHz, CDCl 3 ) S20
21 13 C NMR (300 MHz, CDCl 3) S21
22 1 H NMR (300 MHz, CDCl 3 ) S22
23 13 C NMR (300 MHz, CDCl 3) S23
24 1 H NMR (300 MHz, CDCl 3 ) S24
25 13 C NMR (300 MHz, CDCl 3) S25
26 1 H NMR (300 MHz, CDCl 3 ) S26
27 13 C NMR (300 MHz, CDCl 3) S27
28 1 H NMR (300 MHz, CDCl 3 ) S28
29 13 C NMR (300 MHz, CDCl 3) S29
30 S30
31 13 C NMR (300 MHz, CDCl 3) S31
32 5e 1 H NMR (300 MHz, CDCl 3 ) S32
33 5e 13 C NMR (300 MHz, CDCl 3) S33
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