Palladium(II)-Catalyzed Ortho Arylation of 2-Phenoxypyridines with Potassium Aryltrifluoroborates via C-H Functionalization

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Title:	Palladium(II)-Catalyzed Ortho Arylation of 2-Phenoxypyridines with Potassium Aryltrifluoroborates via C-H Functionalization
Authors:	Jean-Ho Chu (朱見和) Pi-Shan Lin (林碧珊) Ming-Jung Wu (吳明忠)
Date:	2011
Issue Date:	2011-06-23 14:57:43 (UTC+8)
Abstract:	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.
Relation:	2011年台俄有機、藥物與生物化學交流暨藥物化學研討會，起迄日：2011/04/06~2011/04/05，地點：溪頭台大實驗林
Appears in Collections:	[Pharmacy and Science] 2011 Taiwanese-Russian Organic, Medicinal and Bio Chemistry Interactions & PST Medicinal Chemistry Symposium

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