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- W2972237750 abstract "Palladium-catalyzed Suzuki-Miyaura cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on the precise sequence engineering of the catalytic cycle, wherein decarbonylation occurs prior to the transmetallation step. The reaction is compatible with a wide range of boronic acids and amides, providing valuable biaryls in high yields (>60 examples). DFT studies support a mechanism involving oxidative addition, decarbonylation and transmetallation and provide insight into high N-C(O) bond activation selectivity. Most crucially, the reaction establishes the use of palladium catalysis in the biaryl Suzuki-Miyaura cross-coupling of the amide bond and should enable the design of a wide variety of cross-coupling methods in which palladium rivals the traditional biaryl synthesis from aryl halides and pseudohalides." @default.
- W2972237750 created "2019-09-12" @default.
- W2972237750 creator A5007700944 @default.
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- W2972237750 date "2019-01-01" @default.
- W2972237750 modified "2023-10-17" @default.
- W2972237750 title "Palladium-catalyzed decarbonylative Suzuki–Miyaura cross-coupling of amides by carbon–nitrogen bond activation" @default.
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- W2972237750 doi "https://doi.org/10.1039/c9sc03169c" @default.
- W2972237750 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6977462" @default.
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- W2972237750 hasPublicationYear "2019" @default.
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