基于螯合导向C—H/C—H氧化交叉偶联/环化反应策略构筑稠杂芳烃化合物

Chelation-Assisted C—H/C—H Oxidative Cross-Coupling/Cyclization for the Construction of Fused(Hetero)aromatics

稠杂芳烃的合成是有机化学的重要研究内容之一,对有机光电功能材料和器件研究具有重要意义。C—H键是有机化合物中最广泛存在的化学键。利用C—H键的断裂与重组成键直接构筑稠杂芳烃具有简洁、高效的优势,能够解决传统合成方法在底物制备和产物结构类型方面的局限。本文对近六年来,本课题组在基于导向过渡金属催化(杂)芳环与(杂)芳环之间的C—H/C—H氧化交叉偶联/分子内环化反应策略构筑稠(杂)芳环方面所做的系列工作进行了评述,重点讨论了有关反应的特点、优势和催化机理,并对该策略在新型有机光电材料开发中的应用进行了阐述。最后,对该策略目前存在的问题进行了总结,并展望了其发展前景。

The synthesis of fused heteroaromatics is an important research area in organic chemistry and it has significant implications on the investigations of organic optoelectronic materials and devices.C—H bond is one of the most ubiquitous chemical bonds in organic compounds.The direct construction of fused heteroaromatics via the C—H bond cleavage and direct functionalization features concision and high efficiency,which could solve the limitations on the substrate preparation and product structural diversity in conventional synthetic methods.In this account,we review our works on the construction of fused heteroaromatics based on chelation-assisted transition metal-catalyzed oxidative C—H/C—H cross-coupling between(hetero)arenes/intramolecular cyclization during the past six years,including a comprehensive discussion of the features,advantages and reaction mechanisms of these reactions,and the applications of these strategies in the exploration of novel organic optoelectronic materials.Finally,the existing problems and development prospect of this area are elaborated.