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• W2904408312 endingPage "397" @default.
• W2904408312 startingPage "387" @default.
• W2904408312 abstract "Abstract The formation of N-(2'-(diphenylphosphoryl)-[1,1′-biphenyl]-2-yl)-2,3,4,5,6-pentafluorobenzamide (3_eaaa) has been achieved through the palladium-catalyzed and Ag(I)-assisted C H functionalization of N-([1,1′-biphenyl]-2-yl)-2,3,4,5,6-pentafluorobenzamide (1_eaa) via phosphination and in the presence of diphenylphosphine oxide (2_a). The reaction was accompanied with small amount of carbazole derivative, (9H-carbazol-9-yl)(perfluorophenyl)methanone (4_eaa). Crystal structures of 3_eaaa and 4_eaa were both determined by X-ray crystal diffraction methods. Indeed, phosphination took place at the ortho-position of inter-annular ring of 1_eaa. Substituents with various electron-withdrawing/donating capacities on the amido-fragment of 1 were found to greatly affect the ratio distribution of products 3 and 4. By contrast, substituents on various locations of the biphenyl in 1 do not influence much on the outcome of the products distribution. A reaction mechanism is proposed to account for these experimental observations. Computational studies employing Density Functional Theory methods (DFT) on this proposed mechanism found that the electron density property of the palladium metal center in the intermediate II is critical to the formation of either 3 or 4. A relatively electron-poor palladium metal center favors the pathway of forming 3. On the contrary, the pathway of producing 4 will be prevailed while the palladium metal center is having fair amount of electron-density in the proposed intermediate II." @default.
• W2904408312 created "2018-12-22" @default.
• W2904408312 creator A5002926034 @default.
• W2904408312 creator A5007578853 @default.
• W2904408312 creator A5050145639 @default.
• W2904408312 creator A5051209925 @default.
• W2904408312 creator A5070199655 @default.
• W2904408312 creator A5071002659 @default.
• W2904408312 date "2019-01-01" @default.
• W2904408312 modified "2023-10-18" @default.
• W2904408312 title "Palladium-catalyzed phosphination and amination through C H bond functionalization on biphenyl: Amido-substituent as directing group" @default.
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