Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2411-2418.DOI: 10.6023/cjoc202003049 Previous Articles     Next Articles


从屹康, 曾祥华   

  1. 嘉兴学院生物与化学工程学院 浙江嘉兴 314001
  • 收稿日期:2020-03-20 修回日期:2020-05-11 发布日期:2020-05-29
  • 通讯作者: 曾祥华
  • 基金资助:

Nano Cu-CuFe2O4-Catalyzed Selective Reduction of α,β,γ,δ-Unsaturated Carbonyls in Alcohol Medium

Cong Yikang, Zeng Xianghua   

  1. College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001
  • Received:2020-03-20 Revised:2020-05-11 Published:2020-05-29
  • Supported by:
    Project supported by the National Natural Science Foundation of Zhejiang Province (No. LY17B030011).

An efficient Cu-CuFe2O4 nanoparticle-catalyzed protodeboronation strategy has been developed for the chemoselective 1,4-reduction of α,β,γ,δ-unsaturated ketones, carboxylic ester and cyano-ester. This protocol has the advantageous of the use of alcohol as hydrogen source and solvent, low catalyst loading (0.5 mol%), and excellent catalyst recyclability. Additionally, the Cu-CuFe2O4 catalyst has shown excellent performance in gram-scale reactions. Furthermore, the catalytic mechanism has also been discussed. The reactivity of (E)-γ,δ-unsaturated carbonyl products, an important class of γ,δ-unsaturated alkenes, enables easy access to 3-buten-1-ols, 3-buten-1-amines, γ-keto acids, cyclic ethers, and cyclic nitrones.

Key words: α,β,γ,δ-unsaturated carbonyls, nano Cu-CuFe2O4, chemoselective, 1,4-reduction