Sodium Carbonate → HCID 86646876, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL Schlenk flask is charged with 2,6-bis-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (2.00 mmol), 5-bromothiophene-3-carbaldehyde (UkrOrgSynthesis Ltd., Kiev, Ukraine) (5.00 mmol), sodium carbonate (10 mmol), ALIQUAT 336 (0.09 g, a mixture of [CH3(CH2)9]3NCH3+Cl− and [CH3(CH2)7]3NCH3+Cl−, used as a phase transfer catalyst), distilled water (25 mL), and toluene (100 mL). The mixture is degassed under a Schlenk line to remove oxygen. Tetrakis(triphenylphosphine)palladium(0) (0.02 mmol) is then added under nitrogen flow. The mixture is stirred under nitrogen at 90° C. for 20 hours. The upper toluene solution is isolated and washed with DI water (100 mL×3). After being concentrated to about 25 mL, it is quenched in methanol (MeOH) (100 mL). The precipitate is collected by filtration and is purified by zone sublimation or column chromatography (silica gel, chloroform or hexane).

Provenance & Evidence