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TCI Practical Example: C-H Arylation of N-Heteroarene Using a Photoredox Catalyst
We are proud to present the C-H arylation of N-heteroarene catalyzed by Ru(bpy)3Cl2･6H2O.
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Used Chemicals
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Procedure
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Ru(bpy)3Cl2･6H2O (80.1 mg, 0.125 mmol, 2.5 mol%), caffeine (9.71 g, 50.0 mmol, 10 eq.), 4-methoxybenzenediazonium tetrafluoroborate (1.11 g, 5.00 mmol, 1.0 eq.) and formic acid (25 mL) were added to a 100 mL four-necked round bottomed flask at room temperature. The mixture was placed at a distance of 2-3 cm from Blue LED lamps. The brown solution was stirred at rt under visible light irradiation. After 14 hours of irradiation, 5% sodium bicarbonate and dichloromethane were added. The organic layer was washed with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product as a red solid (8.20 g), which was purified by column chromatography on silica gel (hexane:ethyl acetate = 80:20 - 34:66) to afford compound 1 as a pale red solid (632 mg, Y. 42 %).
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Experimenter’s Comments
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The flask was irradiated with 40 W blue LED lamps x 2 (3 cm away, with cooling fans to keep the reaction at room temperature).
The reaction mixture was monitored by 1H NMR.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3); δ 7.62 (d, J = 8.7 Hz, 2H), 7.01 (d, J = 8.7 Hz, 2H), 4.02 (s, 3H), 3.86 (s, 3H), 3.61 (s, 3H), 3.41 (s, 3H).
13C NMR (101 MHz, CDCl3); δ 161.1, 155.5, 152.1, 151.7, 148.2, 130.6, 120.5, 114.3, 108.2, 55.4, 33.9, 29.8, 27.9.
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Lead Reference
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- Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water
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Other Reference
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- Room-Temperature C–H Arylation: Merger of Pd-Catalyzed C–H Functionalization and Visible-Light Photocatalysis