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Gold Catalysis of Non-Conjugated Haloacetylenes
Synthesis ( IF 2.6 ) Pub Date : 2020-11-26 , DOI: 10.1055/s-0040-1706606
Gebhard Haberhauer , Hannah Siera , Nina Semleit , Mathis Kreuzahler , Christoph Wölper

Gold-catalyzed reactions of conjugated haloacetylenes are well known and usually result in the formation of addition or dimerization products. Herein, we report a gold-catalyzed reaction of non-conjugated­ haloacetylenes, which leads exclusively to the halogenated cyclization products. Remarkable is the gold-catalyzed reaction of tritylhaloacetylenes to haloindene derivatives, as mechanistic studies reveal that an 1,2-aryl shift occurs in the initially formed gold complex. The potential functionalization at the halogen atom and the wide scope of these cyclization reactions make them an attractive method for the construction of cyclic systems.



中文翻译:

非共轭卤代乙炔的金催化

共轭卤乙炔的金催化反应是众所周知的,通常会导致加成或二聚产物的形成。在此,我们报告了非共轭卤乙炔的金催化反应,该反应仅导致卤代环化产物。引人注目的是三苯甲基卤乙炔与卤代茚衍生物的金催化反应,因为机理研究表明,在最初形成的金络合物中发生了1,2-芳基移位。卤原子处的潜在官能化和这些环化反应的广泛范围使其成为构建环状体系的有吸引力的方法。

更新日期:2020-11-27
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