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- W2333820121 abstract "The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C–H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications." @default.
- W2333820121 created "2016-06-24" @default.
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- W2333820121 date "2014-02-21" @default.
- W2333820121 modified "2023-10-09" @default.
- W2333820121 title "Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-<i>N</i>-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications" @default.
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- W2333820121 doi "https://doi.org/10.1021/om401195w" @default.
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