An efficient synthesis of ortho-arylated 2-phenoxypyridines catalyzed by palladium acetat#te *s described. Treatment of 2-phenoxypyridmes with two and i a half equivalents of potassium aryltrifluoroborate and 10 mol % of Pd(OAc)2 in the presence of two equivalents of Ag2C03, one equivalent of p-benzoquinone (BQ), and four equivalents of DMSO with (or without) H20 at 130-140 �C for 48 h in dried CH2C12 gave the ortho-arylated 2-phenoxypyridines in modest to excellent yieldds. p-Benzoquinone is found to be an important ligand and co-oxidant for the transmetalation reductive elimination step in the catalytic reaction. The investigatiqon of kinetic isotope effect (kH/kD) is determined to be 5.25, which indicates that compounds, 2-(4'-nitrobiphenyl-2-yloxy)pyridine, was treated with methyl trifluoromethanesulfonate and subsequently sodium methoxide to give the 2-(4- nitrophenyl)phenol in 79% yield, demonstrating that pyridine is a removable directing group.
