General procedure for the Ni-catalyzed cross-electrophile coupling of pyridinium salts with bromoalkynes

An oven-dried 25-ml Schlenk tube equipped with a stir bar was charged with redox-active pyridinium salts 1 (0.2 mmol, 1.0 equiv), 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). 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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