89414-56-2Relevant academic research and scientific papers
An unusual access to medium sized cycloalkynes by a new goId(I)-catalysed cycloisomerisation of diynes
Odabachian, Yann,Le Goff, Xavier F.,Gagosz, Fabien
supporting information; scheme or table, p. 8966 - 8970 (2010/04/25)
A study was conducted to demonstrate efficient cycloisomerization of a series of 1,9- and 1,10-diynes into medium sized cycloalkynes by a gold-catalyzed alkyne-alkyne coupling. The reaction was performed using 4 mol% of gold complex in CD2Cl2 at room temperature and was monitored by using 1H NMR spectroscopy. The reaction of analogous diyne substrate was more rapid and a complete conversion was observed after 40 hours at room temperature. The cycloalkyne was isolated as a solid in 95% yield from which single crystals suitable for X-ray crystal structure determination was obtained. A rapid screening of catalysts and experimental conditions was undertaken to optimize the formation of cycloalkyne. A mechanistic proposal was also introduced for the cycloisomerization of diynes into cycloalkynes on the basis of the experimental observations.
