Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2169-2177.DOI: 10.6023/cjoc201303011 Previous Articles     Next Articles



张明a, 王玲玲a, 李来才a, 田安民b   

  1. a 四川师范大学化学与材料科学学院 成都 610066;
    b 四川大学化学学院 成都 610064
  • 收稿日期:2013-03-08 修回日期:2013-05-03 发布日期:2013-06-21
  • 通讯作者: 李来才
  • 基金资助:

    四川教育厅(No. 13ZA0150)资助项目

Investigation on Coupling Reaction Mechanism from N-(2-Bromophenyl)-2,2,2-trifluoroacetamide and Terminal Alkyne to Indol Catalyzed by CuI

Zhang Minga, Wang Linglinga, Li Laicaia, Tian Anminb   

  1. a College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066;
    b Department of Chemistry, Sichuan University, Chengdu 610064
  • Received:2013-03-08 Revised:2013-05-03 Published:2013-06-21
  • Supported by:

    Project supported by the Department of Education of Sichuan Province (No. 13ZA0150).

The reaction mechanism of N-(2-bromophenyl)-2,2,2-trifluoroacetamide and terminal alkyne catalyzed by CuI has been investigated by using density functional theory. The geometries of the reactants, transition states, intermediates and products have been optimized completely at B3LY P/6-31+G* level with the validation of the vibration analysis and the energy calculation. Atoms in molecules (AIM) theories and nature bond orbital (NBO) have been applied to discuss the orbits interaction and the bond natures. Catalytic mechanism is also interpreted by frontier orbital theory. Two possible reaction paths IA and IB were obtained. The results indicated that IA is the really main possible path of the reaction. Meanwhile, the single point energy of the reaction process in gas and solvent at 6-311+G* level has been individually investigated with higher precision. The results indicate that the reaction mechanism and the change trend of correspondence energy at two different levels are consistent. The final result of the our theory study agrees with the experimental data, and it illustrate that CuI is an effective catalyst in this reaction.

Key words: density functional theory, CuI-catalyze, synthesis of indol, reaction mechanism, frontier orbitals theory