Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization.,The Journal of Organic Chemistry

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Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-10-14 , DOI: 10.1021/acs.joc.9b01644
Vikram Singh ₁ , Ram Subhawan Verma ₁ , Anil K Khatana ₁ , Bhoopendra Tiwari ₁

Affiliation

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

中文翻译：

通过Aryne Diels-Alder反应/芳构化从β-溴乙烯基芳烃构建菲和萘。

已开发出一种高效的无过渡金属的通用方法，该方法可从β-溴乙烯基芳烃和芳烃中合成诸如菲和菲（及四苯）之类的多环芳烃。该反应通过芳烃Diels-Alder（ADA）反应进行，然后进行容易的芳构化。这是有关使用ADA方法直接构建车菊（和四苯酚）的第一份报告。与仅限于9/10取代衍生物的文献方法不同，该方法可使用多种官能化的菲。

更新日期：2019-10-14

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