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首页> 外文期刊>Chemistry: A European journal >Straightforward Synthesis of 5-Bromopenta-2,4-diynenitrile and Its Reactivity Towards Terminal Alkynes: A Direct Access to Diene and Benzofulvene Scaffolds
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Straightforward Synthesis of 5-Bromopenta-2,4-diynenitrile and Its Reactivity Towards Terminal Alkynes: A Direct Access to Diene and Benzofulvene Scaffolds

机译：直接合成5-溴openta-2,4-二炔腈及其对末端炔烃的反应性：直接访问二烯和苯并富烯骨架

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摘要

The high-yielding synthesis of 5-bromopenta-2,4-diynenitrile (BrC5N) was achieved for the first time. Its reactivity with triisopropylsilylacetylene and triisopropylsilylbutadiyne in the presence of copper and palladium as co-catalysts and diisopropylamine was evaluated. It revealed an unprecedented cascade reaction leading to a diene in one case and to a benzofulvene in the other case, with a unique structure. Both of them were characterized by X-ray crystallography, among other techniques. The mechanism of the reaction leading to the diene was investigated experimentally. Theoretical calculations at the DFT level suggest that the mechanism leading to the benzofulvene relies on a hexa-dehydro Diels-Alder (HDDA)-type of mechanism. This work constitutes an example of an unanticipated reactivity leading to an important increase of chemical complexity.
机译：首次实现了5-溴戊-2,4-二炔腈（BrC5N）的高产率合成。在铜和钯作为助催化剂和二异丙胺的存在下，评价了其与三异丙基甲硅烷基乙炔和三异丙基甲硅烷基丁二炔的反应性。它揭示了一种空前的级联反应，在一种情况下会导致二烯，在另一种情况下会导致苯并富勒烯具有独特的结构。除其他技术外，它们都通过X射线晶体学表征。实验研究了生成二烯的反应机理。 DFT级的理论计算表明，导致苯并富勒烯的机理依赖于六脱氢Diels-Alder（HDDA）型机理。这项工作构成了导致化学复杂性显着增加的意外反应性的一个例子。

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