Intermolecular Desymmetrizing Gold-Catalyzed Yne-Yne Reaction of Push-Pull Diarylalkynes

被引:25
作者
Weingand, Vanessa [1 ]
Wurm, Thomas [1 ]
Vethacke, Vanessa [1 ]
Dietl, Martin C. [1 ]
Ehjeij, Daniel [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Xie, Jin [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia
关键词
alkyne dimerization; gold catalysis; naphthalenes; push-pull systems; vinyl cations; TERMINAL ALKYNES; DIYNE REACTION; 1,6-DIYNES; COMPLEXES; ACCESS; CYCLOISOMERIZATION; CYCLIZATIONS; VINYLIDENES; DERIVATIVES; SELECTIVITY;
D O I
10.1002/chem.201800360
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Push-pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.
引用
收藏
页码:3725 / 3728
页数:4
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