Scheme 2.

Pd-catalyzed arylation of methanol-d₄^a

^aReaction conditions: (Het)ArX (1 mmol), CD₃OD (5 mmol), NaO^tBu (1.4 mmol), 3 (2 mol %), L2 (2 mol %), 1,4-dioxane (2 mL, 0.50 M); isolated yields, average of two runs. ^b Cs₂CO₃ (1.5 equiv). ^c After the reaction, the reaction mixture was further heated with H₂O (100 equiv) for 20 min at the reported temperature to form RNHBoc. ^d 3 (1 mol %) and L2 (1 mol %).