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TCI Practical Example: Buchwald-Hartwig Amination of Aryl Chlorides using a Palladium Catalyst and XPhos Ligand
We are going to introduce the Buchwald-Hartwig cross-coupling of aryl chloride utilizing Pd(dba)2 as a catalyst, and XPhos ligand.
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Used Chemicals
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Procedure
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To a 2-necked flask was charged with bis(dibenzylideneacetone)palladium(0) (36 mg, 0.0633 mmol, 1.5 mol%), XPhos (60 mg, 0.127 mmol, 3.0 mol%), sodium tert-butoxide (811 mg, 8.44 mmol, 2.0 equiv.) and toluene (5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 4-chlorotoluene (0.5 mL, 4.22 mmol, 1.0 equiv.), and morpholine (0.55 mL, 6.33 mmol, 1.5 equiv.) were added in one portion. The resulting mixture was stirred at reflux for 6 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane : ethyl acetate = 9 : 1) to afford the corresponding compound 1 as an orange solid (700 mg, 94%).
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Experimenter's Comments
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Toluene was degassed by bubbling with nitrogen gas for 30 min.
The reaction mixture was monitored by GC.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3); δ 7.10 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H), 3.87 (t, J = 4.8 Hz, 4H), 3.11 (t, J = 4.8 Hz, 4H), 2.28 (s, 3H).
13C NMR (101 MHz, CDCl3); δ 149.1, 129.7, 129.5, 116.0, 66.9, 49.9, 20.4.
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Lead Reference
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- Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions
