Potassium (Acetoxymethyl)trifluoroborate

Experimental procedure: To a mixture of 2-chloronaphthalene (1.00 g, 6.15 mmol), Pd(dba)₂ (177 mg, 0.307 mmol), RuPhos (362 mg, 0.738 mmol), sodium carbonate (978 mg, 9.22 mmol) and potassium (acetoxymethyl)trifluoroborate (1.66 g, 9.22 mmol) are added 1,4-dioxane (90 mL) and distilled water (9.0 mL). The reaction mixture is stirred at reflux for 24 h under N₂. The reaction mixture is cooled to room temperature and filtered, and then the filtrate is added water and ethyl acetate. The residue is extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (heptane:ethyl acetate = 4:1) to afford naphthalene-2-yl-methanol (768 mg, 79%).