Fast copper-, ligand- and solvent-free Sonogashira coupling in a ball mill
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- Ζηνόβιος Λύκος
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1 Electronic Supporting Information Fast copper-, ligand- and solvent-free Sonogashira coupling in a ball mill Rico Thorwirth, Achim Stolle * and Bernd ndruschka Institute for Technical Chemistry and Environmental Chemistry, Friedrich-Schiller University Jena, Lessingstraße 12, D Jena, Germany * Fax: (+49) ; bernd.ondruschka@uni-jena.de General information: All chemicals were purchased from Sigma Aldrich or Alfa Aesar and were used as received. Reactions were accomplished in a Fritsch Pulverisette 7 classic line planetary ball mill using 45 ml grinding beakers (agate, zircon oxide) and milling balls (six pieces 15 mm in diameter, agate or zircon oxide). GC-FID measurements were performed on a HP-6890 GC, GC-MS measurements were done on a Agilent Technologies GC 6890N with MS detector 5973 [Conditions GC-FID: HP 5, 30 m 0.32 mm 0.25 µm, H 2 10 psi, program: 70 C (hold for 3 min), 15 K min -1 up to 280 C (hold for 10 min), injector temperature: 280 C, detector temperature: 300 C. Conditions GC-MSD: HP 5, 30 m 0.32 mm 0.25 µm, He 10 psi, program: 70 C (hold for 3 min), 15 K min -1 up to 280 C (hold for 7 min), injector temperature: 280 C, detector: EI]. NMR spectra were recorded with a Bruker Avance 200 MHz system at room temperature in Chloroform-[ 2 H] 3 (CDCl 3 ) as solvent. Reaction Protocol: General procedure for the Sonogashira reaction in planetary ball mill: The grinding beakers were filled with the milling balls, Si2 (5 g), the acetylene compound (2.5 mmol), DABC (2.5 mmol, 280 mg), the aryl halide (2 mmol) and Pd(Ac)2 (5 mol%, 25 mg) were added in the given order. Milling was accomplished at 800 rpm for 20 min. After cooling to room temperature, the crude products were extracted on a frit with a thin silica layer using 1
2 chloroform (3 10 ml). The solvent was evaporated in vacuum, the crude products were dried and analyzed by GC-FID and GC-MS. Analytical samples for NMR investigation were isolated by column chromatography using n-hexane/toluene mixtures. Products were identified according to literature data. NMR data of Sonogashira coupling products: Diphenylethyne (3a): [1] 1 H-NMR (200 MHz, CDCl 3 ): δ = (4 H, m), ppm (6 H, m); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , ppm; GC- MS: m / z= 178 (100%). 1-Methyl-2-(phenylethynyl)benzene (3b): [1] 1 H-NMR (200 MHz, CDCl 3 ): δ = (3 H, m), (3 H, m), (3 H, m), 2.53 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , , 93.32, 88.32, ppm; GC-MS: m / z= 192 (100%). 1-Methyl-4-(phenylethynyl)benzene (3c, 3g): [1] 1 H-NMR (200 MHz, CDCl 3 ): δ = (2 H, m), 7.64 (2 H, d, J = 8.2 Hz), (3 H, m), 7.29 (2 H, d, J = 8.1 Hz), 2.49 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , 89.60, 88.75, ppm; GC-MS: m / z= 192 (100%). 2
3 1-Methoxy-2-(phenylethynyl)benzene (3d): [1] 1 H-NMR (200 MHz, CDCl 3 ): δ = (2 H, m), 7.53 (1 H, dd, J = 7.5, 1.7 Hz), (4 H, m), (2 H, m), 3.90 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , , 93.37, 85.73, ppm; GC-MS: m / z= 208 (100%). 1-Methoxy-4-(phenylethynyl)benzene (3e): [1] 1 H-NMR (200 MHz, CDCl 3 ): δ = (4 H, m), (3 H, m), 6.89 (2 H, d, J = 8.7 Hz), 3.80 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , 89.38, 88.05, ppm; GC-MS: m / z= 208 (100%). 1-Acetyl-4-(phenylethynyl)benzene (3f): [2] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (2 H, d, J = 8.2 Hz), (4 H, m), (3 H, m), 2.47 (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , 92.47, 88.47, ppm; GC-MS: m / z = 220 (100%). 1,2-Di-p-tolylethyne (3h): [2] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.49 (4 H, d, J = 8.1 Hz), 7.22 (4 H, d, J = 7.7 Hz), 2.43 ppm (6 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , 88.90, ppm; GC-MS: m / z = 206 (100%). 1-Methyl-4-(4 -methoxy-phenylethynyl)benzene (3j): [2] 1 H-NMR (200 MHz, CDCl 3 ): δ = (4 H, m), 7.14 (2 H, d, J = 8.0 Hz), (2 H, m), 6.87 (2 H, d, J = 9.0 Hz), 3
4 3.81 (3 H, s), 2.36 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , 88.64, , ppm; GC-MS: m / z = 222 (100%). 1-Acetyl-4-(p-tolyl-ethynyl)benzene (3k): [4] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.85 (2 H, d, J = 8.4 Hz), 7.53 (2 H, d, J = 8.4 Hz), 7.41 (2 H, d, J = 8.0 Hz), 7.10 (2 H, d, J = 8.0 Hz), 2.49 (3 H, s), 2.31 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , 92.77, 87.89, 26.08, ppm; GC-MS: m / z = 234 (100%). 1,2-bis(p-Methoxyphenyl)ethyne (3l): [5] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.49 (4 H, d, J = 8.1 Hz), 7.22 (4 H, d, J = 7.7 Hz), 2.43 ppm (6 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , 88.90, ppm; GC-MS: m / z = 238 (100%). 1-Acetyl-4-(4 -methoxy-phenylethynyl)benzene (3m): [5] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (2 H, d, J = 8.2 Hz), 7.49 (2 H, d, J = 8.5 Hz), 7.41 (2 H, d, J = 8.7 Hz), 6.80 (2 H, d, J = 8.7 Hz), 3.72 (3 H, s), 2.49 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , 92.83, 87.39, 55.01, ppm; GC- MS: m / z = 206 (100%); GC-MS: m / z = 250 (100%). F 1-Fluoro-4-(4 -methoxy-phenylethynyl)benzene (3n): [6] 1 H-NMR (200 MHz, CDCl 3 ): δ = (4 H, m), 7.01 (2 H, t, J = 8.8 Hz), 6.86 (2 H, d, J = 8.9 Hz), 3.81 ppm (3 H, s); 13 C- NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , , , , 88.67, 86.62, ppm; GC-MS: m / z = 226 (100%). 4
5 F 1-Acetyl-4-(4 -fluoro-phenylethynyl)benzene (3o): [6] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.86 (2 H, d, J = 8.5 Hz), (4 H, m), 6.99 (2 H, t, J = 8.8 Hz), 2.52 ppm (3 H, s); 13 C- NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , , , , 91.43, 88.23, ppm; GC-MS: m / z = 238 (100%). F 3 C 1-Trifluoromethyl-4-(phenylethynyl)benzene (3p): [7] 1 H-NMR (200 MHz, CDCl 3 ): δ = (4 H, m), (3 H, m), 7.29 ppm (2 H, t, J = 3.2 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = 131.4, , , , , , , , , 91.39, ppm; GC-MS: m / z = 192 (100%). 2 N 1-Nitro-4-(phenylethynyl)benzene (3q): [8] 1 H-NMR (200 MHz, CDCl 3 ): δ = 8.15 (2 H, d, J = 8.9 Hz), 7.61 (2 H, d, J = 8.3 Hz), (3 H, m), ppm (2 H, m); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , 94.45, ppm; GC-MS: m / z = 223 (100%). S 2-Phenylethynylthiophene (5): [3] 1 H-NMR (200 MHz, CDCl 3 ): δ = (2 H, m), (5 H, m), ppm (1 H, m); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , 93.03, ppm; GC-MS: m / z = 184 (100%). 5
6 1-(4-Methoxyphenyl)-dec-1-yne (7a): [3] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.31 (2 H, d, J = 8.8 Hz), 6.79 (2 H, d, J = 8.8 Hz), 3.78 (3 H, s), 2.36 (2 H, t, J = 6.9 Hz), (12 H, m), 0.87 (3 H, t, J = 6.5 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , 88.80, 80.22, 55.22, 31.83, 29.18, 29.12, 28.93, 28.87, 22.64, 19.34, ppm; GC-MS: m / z = 244 (100%). 1-(4-Acetylphenyl)-dec-1-yne (7b): [3] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.73 (2 H, d, J = 8.1 Hz), 7.31 (2 H, d, J = 8.2 Hz), 2.42 (3 H, s), 2.30 (2 H, t, J = 6.9 Hz), (12 H, m), 0.78 (3 H, t, J = 6.6 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , 93.95, 79.89, 31.57, 28.84, 28.67, 28.33, 26.02, 22.38, 19.22, ppm; GC-MS: m / z = 256 (100%). 1-(4-Methoxyphenyl)-dodec-1-yne (7c): [9] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.33 (2 H, d, J = 8.8 Hz), 6.79 (2 H, d, J = 8.8 Hz), 3.76 (3 H, s), 2.38 (2 H, t, J = 6.8 Hz), (16 H, m), 0.90 (3 H, t, J = 6.6 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , 88.53, 80.24, 54.96, 31.88, 29.56, 29.31, 29.15, 28.88, 22.64, 19.34, ppm; GC- MS: m / z = 272 (100%). 1-(4-Acetylphenyl)-dodec-1-yne (7d): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.73 (2 H, d, J = 8.2 Hz), 7.32 (2 H, d, J = 8.3 Hz), 2.42 (3 H, s), 2.29 (2 H, t, J = 6.9 Hz), (16 H, m), 0.78 (3 H, t, J = 6.7 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , 93.99, 79.93, 31.69, 29.37, 29.11, 28.93, 28.72, 28.38, 26.07, 22.45, 19.27, ppm; GC-MS: m / z = 284 (100%). 6
7 H 4-(4-Acetylphenyl)-2-methylbut-3-yn-2-ol (9a): [10] 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (2 H, d, J = 8.3 Hz), 7.43 (2 H, d, J = 8.4 Hz), 2.53 (3 H, s), 2.43 (1 H, bs), 1.61 ppm (6 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , 93.95, 83.54, 68.81, 30.46, ppm; GC-MS: m / z = 202 (100%). H 5-(4-Acetylphenyl)-3-methyl-pent-1-en-4-yn-3-ol (9b): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (2 H, d, J = 8.3 Hz), 7.44 (2 H, d, J = 8.5 Hz), 6.03 (1 H, dd, J = 10.2 Hz, J = 17.1 Hz), 5.53 (1 H, dd, J = 0.9 Hz, J = 17.1 Hz), 5.13 (1 H, dd, J = 0.9 Hz, J = 10.2 Hz), 2.78 (1 H, bs), 2.54 (3 H, s), 1.63 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , 94.36, 83.70, 68.47, 29.90, ppm; GC-MS: m / z = 214 (100%). H 1-(4-Acetylphenyl)-3,7-dimethyl-oct-6-en-1-yn-3-ol (9c): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (2 H, d, J= 8.3 Hz), 7.43 (2 H, d, J= 8.3 Hz), 5.16 (1 H, t, J = 7.2 Hz), 2.54 (3 H, s), 2.45 (1 H, bs), (2 H, m), 1.76 (2 H, t, J = 7.5 Hz), 1.65 (3 H, s), 1.61 (3 H, s), 1.54 ppm (3 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , 96.29, 82.66, 68.71, 43.31, 29.68, 26.47, 25.62, ppm; GC-MS: m / z = 270 (100%). 7
8 1,3-(4-Acetylphenyl)benzene (11a): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.92 (4 H, d, J = 8.6 Hz), (1 H, m), 7.58 (4 H, d, J = 8.6 Hz), (2 H, m), 7.34 (1 H, t, J = 7.7 Hz), 2.59 ppm (6 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , , , 91.57, 89.35, ppm. 1,4-(4-Acetylphenyl)benzene (11b): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.94 (4 H, d, J = 8.5 Hz), 7.60 (4 H, d, J = 8.4 Hz), 7.53 (4 H, s), 2.60 ppm (6 H, s); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , , , 91.18, 88.78, ppm. 1,8-(4-Acetylphenyl)oct-1,7-diyne (11c): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.83 (4 H, d, J = 8.5 Hz), 7.42 (4 H, d, J = 8.5 Hz), 2.54 (6 H, s), 2.48 (4 H, t, J = 6.5 Hz), 1.77 ppm (4 H, q, J = 3.2 Hz); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , 93.52, 80.48, 27.64, 26.50, ppm. 1,9-(4-Acetylphenyl)non-1,8-diyne (11d): 1 H-NMR (200 MHz, CDCl 3 ): δ = 7.80 (4 H, d, J = 8.3 Hz), 7.40 (4 H, d, J = 8.3 Hz), 2.54 (6 H, s), 2.45 (4 H, t, J = 6.1 Hz), (6 H, m); 13 C-NMR (50 MHz, CDCl 3 ): δ = , , , , , 93.58, 80.08, 27.67, 27.62, 26.17, ppm. 8
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