Application
Ester-amide Exchange Reactions of Vinyl Esters Using N-Heterocyclic Carbene (NHC) Catalysts
Experimental procedure:
A suspension of potassium tert-butoxide (2.8 mg, 0.025 mmol) and IMes·HCl (10.2 mg, 0.03 mmol) in anhydrous toluene (1.0 mL) is stirred at ambient temperature for 0.5 h. A vinyl ester (0.5 mmol) and an amine (0.75 mmol) are added subsequently and the solution is stirred at 60 °C. The crude mixture is purified by flash silica gel column chromatography to give the desired product.
References
- N-Heterocyclic carbene-catalysed amidation of vinyl esters with aromatic amines
Application
NHC-catalyzed Difluorocarbene Generation and Aryl Difluoromethyl Ether Synthesis
Typical Procedure (Entry 2):
To a toluene solution (0.4 mL) of 1,3-dimesitylimidazolium chloride (IMes·HCl) (2.7 mg, 0.0079 mmol), sodium carbonate (8.5 mg, 0.080 mmol), and 6,7-dimethyl-α-tetralone (70 mg, 0.40 mmol) is added trimethylsilyl difluoro(fluorosulfonyl)acetate (100 µL, 0.48 mmol) at room temperature. The reaction mixture is stirred and heated at 80 °C for 1 h. After cooling the resulting mixture to room temperature, DDQ (182 mg, 0.80 mmol) and toluene (2 mL) are added and the mixture is heated at 100 °C for 2 h. Purification by column chromatography (SiO2, hexane) gives the desired product (82 mg, Y. 91%) as a colorless liquid.
References
- N-Heterocyclic carbene-catalyzed difluorocarbene generation and its application to aryl difluoromethyl ether synthesis
Application
Regioselectivity-Switchable Hydroarylation of Styrenes
Reference
PubMed Literature