Scheme 1. Optimization conditions for palladium-catalyzed difluoromethylation of 3-((benzyloxy)methyl)-5-bromopyridine. ^aReaction condition: 3a (27.7 mg, 0.1 mmol), (SIPr)Ag(CF₂H) 2 (55 mg, 0.1 mmol), [Pd] (5 mol%) and ligand (10 mol%) in 1.0 mL toluene for 6 h under Ar atmosphere; ^byields were determined by ¹⁹F NMR analysis of the crude reaction mixture with trifluorotoluene as an internal standard; ^c1.3 equiv. of (SIPr)Ag(CF₂H) was used; ^d[Pd] (2.0 mol%) and DPEPhos (4.0 mol%).