Since the prediction of the existence of metallabenzenes in 1979, metallaaromatic chemistry has developed rapidly, due to its importance in both experimental and theoretical fields. Now six major types of metallaromatic compounds, metallabenzenes, metallabenzynes, heterometallaaromatics, dianion metalloles, metallapentalenes and metallapentalynes (also termed carbolongs), and spiro metalloles, have been reported and extensively studied. Their parent organic analogues may be aromatic, non-aromatic, or even anti-aromatic. These unique systems not only enrich the large family of aromatics, but they also broaden our understanding and extend the concept of aromaticity. This review provides a comprehensive overview of metallaaromatic chemistry. We have focused on not only the six major classes of metallaaromatics, including the main-group-metal-based metallaaromatics, but also other types, such as metallacyclobutadienes and metallacyclopropenes. The structures, synthetic methods, and reactivities are described, their applications are covered, and the challenges and future prospects of the area are discussed. The criteria commonly used to judge the aromaticity of metallaaromatics are presented.

中文翻译：

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金属芳香化学：历史与发展

自从1979年预测金属甲苯的存在以来，由于金属甲芳烃化学在实验和理论领域的重要性，其发展迅速。现在，已经报道并广泛研究了六种主要类型的金属金属化合物，金属苯，金属戊烯酮，杂金属芳烃，二价阴离子金属，金属戊烯和金属戊二烯（也称为卡波隆）和螺金属。它们的母体有机类似物可以是芳香族，非芳香族甚至抗芳香族的。这些独特的系统不仅丰富了庞大的芳香族产品，而且拓宽了我们的理解范围并扩展了芳香性的概念。这篇综述提供了金属芳香化学的全面概述。我们不仅关注六大类的金属芳香族化合物，包括主要的金属基金属芳香族化合物，也包括其他类型，例如金属环丁二烯和金属环丙烯。描述了结构，合成方法和活性，涵盖了它们的应用，并讨论了该领域的挑战和未来前景。介绍了通常用于判断金属芳香族化合物芳香性的标准。