Nano-Cu(2)O-catalyzed formation of C-C and C-O bonds: one-pot domino process for regioselective synthesis of α-carbonyl Furans from electron-deficient alkynes and 2-yn-1-ols.
The formation of carbon-carbon and carbon-oxygen bonds continues to be an active and challenging field of chemical research. Nanoparticle catalysis has attracted considerable attention owing to its environmentally benign and high activity toward the reactions. Herein, we described a novel and effective nano-Cu(2)O-catalyzed one-pot domino process for the regioselective synthesis of α-carbonyl furans. Various electron-deficient alkynes with 2-yn-1-ols underwent this process smoothly in moderate to good yields in the presence of air at atmospheric pressure. It is especially noteworthy that a novel 2,4,5-trisubstituted 3-ynylfuran was formed in an extremely direct manner without tedious stepwise synthesis. Additionally, as all of the starting materials are readily available, this method may allow the synthesis of more complex α-carbonyl furans. An experiment to elucidate the mechanism suggested that the process involved a carbene intermediate.
Cao
Hua
H
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, PR of China.
Jiang
Huanfeng
H
Yuan
Gaoqing
G
Chen
Zhengwang
Z
Qi
Chaorong
C
Huang
Huawen
H