Journal
CHEMICAL SCIENCE
Volume 10, Issue 42, Pages 9865-9871Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc03169c
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Funding
- NSF [CAREER CHE-1650766]
- NSFC [21702182, 21873081]
- Fundamental Research Funds for the Central Universities [2019QNA3009]
- Zhejiang University
- NSF-MRI grant [CHE-1229030]
- Rutgers University
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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.
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