Scheme 4. Pd-catalyzed C–O cross-coupling of aryl bromides with secondary alcohols.^a.

^aReaction conditions: ArBr (1.0 mmol), alcohol (2.0 mmol), NaOt-Bu (1.2 mmol), P2 (2.0–2.5 mol %), THF (1.0 mL, 1.0 M), rt, 18 h. Isolated yields represent the average result of two runs. ^b1.5 equiv of alcohol. ^cTHF (5.0 mL) and higher temperature were used due to the poor solubility of the combination of aryl chloride, alcohol and NaOt-Bu under standard reaction conditions.