| 56% |
With 4-dimethylaminopyridine; 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridin-10-ium tetrafluoroborate In methanol; propan-2-one for 1h; Sealed tube; Inert atmosphere; Irradiation; Green chemistry; |
General procedure for Giese reaction in batch
An oven dried 5-mL microwave tube equipped with a magnetic stirring bar was charged with [4-(4- ethoxyphenyl)phenyl]boronic acid 1a (40 mg, 0.165 mmol), photoredox catalyst (Mes-Acr; 2.6 mg, 0.004 mmol), DMAP (5.0 mg, 0.041 mmol). The vial was sealed with a septum and 3 cycles vacuum/Argon were performed. A 1:1 acetone/MeOH solvent mixture (purged with argon for 15 minutes) (2 mL), and methylviny ketone 2a (46 mg, 0.660 mmol) were added. The tube was irradiated with Penn PhD Photoreactor M2 (450 nm) for 1 h. The reaction, assayed by HPLC/MS, was concentrated in vacuo, reconstituted in DCM, and purified through flash chromatography (AcOEt/Hexane: 0% for 4 CV then to 90% in 12 CV). 4-[4-(4-ethoxyphenyl)phenyl]butan-2-one 3aa was isolated as white solid (25 mg, y: 56 %). 4-(4'-ethoxybiphenyl-4-yl)butan-2-one (3aa) HPLC: Rt 3.53 min 1H-NMR (500 MHz, DMSO-d6) ppm 7.55 (d, J=8.85 Hz, 2 H), 7.50 (d, J=8.24 Hz, 2 H), 7.25 (d, J=8.24 Hz, 2 H), 6.98 (d, J=8.85 Hz, 2 H), 4.05 (q, J=7.02 Hz, 2 H), 2.72 - 2.84 (m, 4 H), 2.10 (s, 3 H), 1.34 (t, J=7.02 Hz, 3 H). 13C-NMR (125.7 MHz, DMSO-d6) ppm: 14.69, 28.65, 29.77, 44.17, 63.06, 114.78, 126.04, 127.52, 128.73, 132.29, 137.47, 139.85, 157.97, 207.72 |
| 1: 51 %Chromat.
2: 49 %Chromat. |
With 4-dimethylaminopyridine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In methanol; propan-2-one for 1h; Sealed tube; Inert atmosphere; Irradiation; Green chemistry; |
General procedure for Giese reaction in batch
An oven dried 5-mL microwave tube equipped with a magnetic stirring bar was charged with [4-(4- ethoxyphenyl)phenyl]boronic acid 1a (40 mg, 0.165 mmol), photoredox catalyst (Mes-Acr; 2.6 mg, 0.004 mmol), DMAP (5.0 mg, 0.041 mmol). The vial was sealed with a septum and 3 cycles vacuum/Argon were performed. A 1:1 acetone/MeOH solvent mixture (purged with argon for 15 minutes) (2 mL), and methylviny ketone 2a (46 mg, 0.660 mmol) were added. The tube was irradiated with Penn PhD Photoreactor M2 (450 nm) for 1 h. The reaction, assayed by HPLC/MS, was concentrated in vacuo, reconstituted in DCM, and purified through flash chromatography (AcOEt/Hexane: 0% for 4 CV then to 90% in 12 CV). 4-[4-(4-ethoxyphenyl)phenyl]butan-2-one 3aa was isolated as white solid (25 mg, y: 56 %). 4-(4'-ethoxybiphenyl-4-yl)butan-2-one (3aa) HPLC: Rt 3.53 min 1H-NMR (500 MHz, DMSO-d6) ppm 7.55 (d, J=8.85 Hz, 2 H), 7.50 (d, J=8.24 Hz, 2 H), 7.25 (d, J=8.24 Hz, 2 H), 6.98 (d, J=8.85 Hz, 2 H), 4.05 (q, J=7.02 Hz, 2 H), 2.72 - 2.84 (m, 4 H), 2.10 (s, 3 H), 1.34 (t, J=7.02 Hz, 3 H). 13C-NMR (125.7 MHz, DMSO-d6) ppm: 14.69, 28.65, 29.77, 44.17, 63.06, 114.78, 126.04, 127.52, 128.73, 132.29, 137.47, 139.85, 157.97, 207.72 |
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