Benzocyclobutadienes: An Unusual Mode of Access Reveals Unusual Modes of Reactivity,Angewandte Chemie International Edition

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Benzocyclobutadienes: An Unusual Mode of Access Reveals Unusual Modes of Reactivity
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-07-04 , DOI: 10.1002/anie.201803872
Xiao Xiao ₁ , Brian P Woods ₁ , Wen Xiu ₁ , Thomas R Hoye ₁

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The reaction of an aryne with an alkyne to generate a benzocyclobutadiene (BCB) intermediate is rare. We report here examples of this reaction, revealed by Diels–Alder trapping of the BCB by either pendant or external electron‐deficient alkynes. Mechanistic delineation of the reaction course is supported by DFT calculations. A three‐component process joining the benzyne first with an electron‐rich and then with an electron‐poor alkyne was uncovered. Reactions in which the BCB functions in a rarely observed role as a 4π diene component in Diels–Alder reactions are reported. The results also shed new light on aspects of the hexadehydro‐Diels–Alder reaction used to generate the benzynes.

中文翻译：

苯并环丁二烯：一种不寻常的获取方式揭示了不寻常的反应模式

芳炔与炔烃反应生成苯并环丁二烯 (BCB) 中间体的情况很少见。我们在这里报道了这种反应的例子，通过侧链或外部缺电子炔烃对 BCB 的 Diels-Alder 捕获揭示了这一点。DFT 计算支持反应过程的机理描述。发现了一种三组分过程，首先将苯与富电子炔烃连接，然后与贫电子炔烃连接。据报道，BCB 在 Diels-Alder 反应中作为 4π 二烯组分发挥着罕见的作用。这些结果还为用于生成苯炔的十六氢-狄尔斯-阿尔德反应的各个方面提供了新的线索。

更新日期：2018-07-04

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