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An unusual access to medium sized cycloalkynes by a new goId(I)-catalysed cycloisomerisation of diynes

Abstract : 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.
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https://hal-polytechnique.archives-ouvertes.fr/hal-00951264
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Submitted on : Sunday, March 2, 2014 - 6:37:22 PM
Last modification on : Friday, February 4, 2022 - 9:02:01 AM

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yann Odabachian, X. F Le Goff, Fabien Gagosz. An unusual access to medium sized cycloalkynes by a new goId(I)-catalysed cycloisomerisation of diynes. Chemistry - A European Journal, Wiley-VCH Verlag, 2009, 15 (36), pp.8966-8970. ⟨10.1002/chem.200901312⟩. ⟨hal-00951264⟩

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