Cross-coupling with iodobenzene. A culture tube was charged with primary amines (0.1 mmol) and 2,4,6-triphenylpyrylium tetrafluoroborate (1.2 equiv). EtOH (1.0 ml) was added, and the culture tube was sealed. The mixture was stirred at 100°C overnight. After that, EtOH was removed under vacuum. NiBr2•diglyme (0.02 mmol), 2,2′:6′,2″-terpyridine (0.02 mmol), zinc flake (−325 mesh, 99.9%) (0.5 mmol), iodobenzene (0.3 mmol), and anhydrous DMF (2 ml) were added under argon. The resulting mixture was allowed to stir for 8 hours under argon atmosphere at 60°C (oil bath). The reaction mixture was quenched with 1 M HCl and extracted with EtOAc. The organic layer was washed with water and brine and dried over Na2SO4. The organic layer was concentrated under vacuum by rotary evaporator in a water bath at 45°C. Flash column chromatography or preparative TLC provided the product.

Cross-coupling with bromoalkynes. A culture tube was charged with 0.1 mmol primary amines (1.0 equiv) and 2,4,6-triphenylpyrylium tetrafluoroborate (1.2 equiv). EtOH (1.0 ml) was added, and the mixture was refluxed overnight. After that, EtOH was removed under vacuum. Ni(acac)2 (0.02 mmol), 4-4′-di-tert-butyl-2,2′-bipyridine (0.02 mmol), and zinc flake (−325 mesh, 99.9%) (0.5 mmol) were added. The tube was then evacuated and back-filled with argon (three times). Anhydrous DMF (1 ml) and bromoalkynes (0.3 mmol) were added under argon. The resulting mixture was allowed to stir for 8 hours under argon atmosphere at 60°C (oil bath). The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine and dried over Na2SO4. The organic layer was concentrated under vacuum by rotary evaporator in a water bath at 45°C. Flash column chromatography provided the product.

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