Theoretical study on Au(I)-catalyzed [2+2+2] cycloadditions of ynamides with two discrete nitriles

被引：19
|
作者：
Liang, Haosheng [1 ]
Bi, Siwei [1 ]
Liu, Yuxia [1 ]
Tang, Ya-nan [1 ]
Liu, Congcong [1 ]
机构：
[1] Qufu Normal Univ, Coll Chem & Chem Engn, Qufu 273165, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 09期
基金：
中国国家自然科学基金;
关键词：
EFFECTIVE CORE POTENTIALS; AB-INITIO; MOLECULAR CALCULATIONS; ENANTIOSELECTIVE SYNTHESIS; CATALYZED CYCLOADDITION; DENSITY FUNCTIONALS; CHEMICAL-REACTIONS; FREE-ENERGIES; C-C; ALKYNES;
D O I：
10.1039/c5ob02568k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Au-catalyzed [2 + 2 + 2] cycloadditions of ynamides with two discrete nitriles were theoretically studied with the aid of DFT calculations. The reaction under consideration is found to start from binding of the catalyst with the ynamide rather than with the nitrile. The Au(I)-ynamide species (1) can effectively induce dimerization of two nitrile molecules while the catalyst only cannot. The Au(I)-ynamide species (1) is revealed to be more reactive than the Au(I)-nitrile species (2). Also, the regioselectivity and the influence of EWG vs. EDG involved in the reaction were also rationalized.
引用
收藏
页码：2637 / 2644
页数：8
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