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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Direct C-N Coupling of Aromatic Aldehydes with Amines by H2O2 for Synthesis of Amides at Room Temperature
Meng-Yun Zhao1, Meng-Han Li1, Guo-Zhi Han1
1College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. China.
Abstract:
In this paper, we report a new mild and environmentally friendly approach for the direct C-N coupling of aromatic aldehydes with amines at room temperature to synthesize amides in which H2O2 serves as the oxidizing agent without the need for a catalyst. Investigation into substrate scope showed that the strategy exhibits good functional group tolerance. Under the optimal reaction conditions, the direct C-N coupling of aromatic aldehydes with secondary amines affords a series of amide products with moderate to high yields of 67%-95%, along with the sole byproduct of water. Additionally, a maximum isolated yield of 90% is achieved in the gram-scale reaction. Finally, a plausible reaction mechanism is proposed via a series of parallel experiments.
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