The Influence of the Quinoline Moiety on Direct Pd‐Catalyzed Arylation of Five‐Membered Heterocycles,European Journal of Organic Chemistry

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The Influence of the Quinoline Moiety on Direct Pd‐Catalyzed Arylation of Five‐Membered Heterocycles
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2018-08-17 , DOI: 10.1002/ejoc.201800842
Bogdan Štefane ₁ , Uroš Grošelj ₁ , Jurij Svete ₁ , Franc Požgan ₁ , Drago Kočar ₁ , Helena Brodnik Žugelj ₁

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Herein we report a study on the reactivity of C2‐quinoline‐substituted furan, thiophene and pyrrole derivatives in palladium‐catalyzed direct C–H arylation. The regioselectivity of the reaction was strongly influenced by site position of the attached five‐membered heterocycle thus giving rise to C3‐ and/or C5‐arylated products. Furthermore, the Hammett correlation performed on 5‐substituted‐8‐(furan‐2‐yl)quinolines indicates that a marginally positive charge is building up in the rate determining transition state and thus pointing towards the electrophilic metalation‐deprotonation reaction mechanism.

中文翻译：

喹啉部分对五元杂环直接Pd催化的芳构化的影响

本文中我们报道了在钯催化的直接CHH芳基化反应中，C2-喹啉取代的呋喃，噻吩和吡咯衍生物的反应性。反应的区域选择性受到连接的五元杂环的位置的强烈影响，因此产生了C3和/或C5芳基化产物。此外，对5-取代-8-（呋喃-2-基）喹啉进行的哈米特相关性表明，在决定速率的过渡态中会形成少量的正电荷，从而指向亲电子的金属化-去质子化反应机理。

更新日期：2018-09-17

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