Application
Catalytic Decarboxylative Cross-Coupling of Aryl Chlorides and Benzoates
Typical Procedure:
An oven-dried, nitrogen-flushed 20 mL crimp cap vessel is charged with the potassium carboxylate (0.60 mmol, 1.2 eq.), (MeCN)4Pd(OTf)2 (5.7 mg, 0.01 mmol, 2.0 mol%), XPhos (12.3 mg, 0.025 mmol, 5.0 mol %), copper(I) iodide (9.7 mg, 0.05 mmol, 10.0 mol%), 3,4,7,8-tetramethyl-1,10-phenanthroline (11.9 mg, 0.05 mmol, 10.0 mol%), and aryl chloride (0.5 mmol). A degassed mixture of NMP (2.5 mL) and quinoline (2.5 mL) is added via syringe. The resulting solution is then stirred at 190 °C for 16 h. After the reaction is complete, the mixture is cooled to room temperature, diluted with 1N HCl and extracted with ethyl acetate (3×50 mL). The combined organic layers are washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified by column chromatography (SiO2, ethyl acetate/cyclohexane gradient) yielding the corresponding product.
References
Application
Trifluoromethylthiolation via Palladium-catalyzed Directed C–H Bond Activation
Reference
- Palladium-Catalyzed Trifluoromethylthiolation of Aryl C?H Bonds
PubMed Literature