Electro-catalytic multicomponent reaction toward asymmetrical biaryls through heteroarylation of in situ generated fused polycyclic heteroaromatics

Wenjing Guan; Jinlin Hang; Yaqi Qiao

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Electro-catalytic multicomponent reaction toward asymmetrical biaryls through heteroarylation of in situ generated fused polycyclic heteroaromatics

机译：Electro-catalytic multicomponent reaction toward asymmetrical biaryls through heteroarylation of in situ generated fused polycyclic heteroaromatics

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摘要

Biaryls have a wide range of applications in medicines, natural products, materials and ligands for metal catalysts. However, it is a huge challenge to achieve the selective cross-coupling between two different heteroarenes compared to homo-coupling. Moreover, the cross-coupling between different heteroarene groups is usually confined to two simple heteroarenes, which sacrifices the richness of products. Herein, we report a straightforward electrosynthesis of highly complex and asymmetrical biheterocyclic hydrocarbons through sequential site-selective cyclization and cross-coupling of in situ generated fused poly-cyclic heteroaromatics under metal-, oxidant-, and additive-free conditions. This sustainable and green methodology features mild reaction conditions, excellent H2O and air tolerance, high atom economy and step economy and good functional group compatibility. Moreover, a possible mechanism has been proposed on the basis of radical-trapping, isotope labeling, KIE, verification of intermediates and cyclic vol-tammetry experiments.

机译：Biaryls有广泛的应用药品、天然产品、材料和配体对金属催化剂。巨大的挑战实现选择性两个不同的heteroarenes之间的交叉耦合而homo-coupling。不同heteroarene之间的交叉耦合组织通常局限于两个简单heteroarenes,牺牲的丰富性产品。电合成的高度复杂的和不对称biheterocyclic碳氢化合物通过顺序site-selective环化和交叉耦合的原位生成的融合poly-cyclic杂芳族化合物在金属,氧化剂和精细的条件。可持续发展和绿色温和的方法论特征反应条件,优秀的水和空气宽容、高经济和原子经济和步骤良好的官能团兼容性。提出了基于可能的机制KIE radical-trapping,同位素标记,验证的中间体和循环vol-tammetry实验。

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来源
《Catalysis science & technology》 |2023年第11期|2790-2797|共8页
作者
Wenjing Guan; Jinlin Hang; Yaqi Qiao;
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College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 211816, China.;

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中图分类物理化学（理论化学）、化学物理学;
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Electro-catalytic multicomponent reaction toward asymmetrical biaryls through heteroarylation of in situ generated fused polycyclic heteroaromatics

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