Department of Chemistry and Pharmacy, Organic Chemistry II, Nikolaus-Fiebiger Str. 10, 91058, Erlangen, Germany.
Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Strasse 2, 06120, Halle (Saale), Germany.
Chemistry. 2021 Dec 9;27(69):17322-17325. doi: 10.1002/chem.202103098. Epub 2021 Nov 10.
Herein, we report a new method for synthesis of extended perylenes and terrylenes. The technique is based on the cascade dehydrative π-extensions (DPEX) of aryl aldehydes, in which stepwise annulations activate previously "dormant" substituents. Two- and fourfold cyclizations of 3-aryl-biphenyl-2,2'-dicarbaldehydes offer a rapid path to unsymmetrical perylenes and elusive terrylene derivatives, respectively. DPEX of 3,3''-(phenanthrene-1,8-diyl)bis (([1,1'-biphenyl]-2,2'-dicarbaldehyde)) leads to the biradical structure, which proceeds in situ into oxidative electrocyclization at room temperature. The described domino process complements and expands DPEX approach to a large family of fused acenes and related PAHs.
在此，我们报告了一种合成扩展的并五苯和苝的新方法。该技术基于芳基醛的级联脱水 π-扩展（DPEX），其中逐步环合激活以前“休眠”的取代基。3-芳基联苯-2,2'-二醛的二聚和四聚环化分别提供了快速合成不对称并五苯和难以获得的苝衍生物的途径。3,3''-（菲-1,8-二基）双（（[1,1'-联苯]-2,2'-二醛））的 DPEX 导致双自由基结构，该结构在原位进行室温下的氧化电环化。所描述的多米诺过程补充并扩展了 DPEX 方法，使其适用于一大类稠合芳烃和相关的多环芳烃。
