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- W2058792806 abstract "An efficient synthesis of ortho-arylated 2-phenoxypyridines catalyzed by palladium acetate is described. Treatment of 2-phenoxypyridines with two and a half equivalents of potassium aryltrifluoroborate and 10 mol % of Pd(OAc)2 in the presence of two equivalents of Ag2CO3, one equivalent of p-benzoquinone (BQ), and four equivalents of DMSO with (or without) H2O at 130−140 °C for 48 h in dried CH2Cl2 gave the ortho-arylated 2-phenoxypyridines in modest to excellent yields. p-Benzoquinone is found to be an important ligand and co-oxidant for the transmetalation reductive elimination step in the catalytic reaction. The investigation of kinetic isotope effect (kH/kD) is determined to be 5.25, which indicates that C−H bond cleavage occurs in the rate-determining step. One of the arylated 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." @default.
- W2058792806 created "2016-06-24" @default.
- W2058792806 creator A5025433626 @default.
- W2058792806 creator A5065455166 @default.
- W2058792806 creator A5085711943 @default.
- W2058792806 date "2010-08-25" @default.
- W2058792806 modified "2023-10-17" @default.
- W2058792806 title "Palladium(II)-Catalyzed <i>Ortho</i> Arylation of 2-Phenoxypyridines with Potassium Aryltrifluoroborates via C−H Functionalization" @default.
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- W2058792806 doi "https://doi.org/10.1021/om100494p" @default.
- W2058792806 hasPublicationYear "2010" @default.
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