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.

Metallaaromatic Chemistry: History and Development.

Metallaaromatics can be broadly defined as aromatic compounds in which one of the ring atoms is a transition metal. The metallabenzenes are one important class of these compounds that has undergone extensive study recently. Closely related species such as fused-ring metallabenzenes, heterometallabenzenes, π-coordinated metallabenzenes and metallabenzynes have also attracted considerable attention. Although many metallaaromatics can be considered as metalla-analogues of classic organic aromatic compounds, this is not always the case. Recent seminal studies have shown that metallapentalenes and metallapentalynes, which are metalla-analogues of the anti-aromatic compounds pentalene and pentalyne, are in fact aromatic and highly stable. Very unusual spiro-metallaaromatic compounds have also recently been isolated. In this concepts article, key features of all these intriguing metallaaromatic compounds are discussed with reference to the structural, spectroscopic, reactivity and theoretical studies that have been undertaken. These compounds continue to generate much interest, not only because of the contributions they make to fundamental chemical understanding, but also because of the promise of possible practical applications.

Recent Advances in Metallaaromatic Chemistry.

Fused-ring metallabenzenes

Cycloamination strategies for renewable N-heterocycles

Aromatic diosmatricyclic nitrogen-containing compounds are prepared from Os(VI) complex OsH6(PiPr3) by double 1,3-C−H bond activation of aromatic six-membered cycles with imino substituents meta disposed.

Aromatic Diosmatricyclic Nitrogen-Containing Compounds

Synthesis and characterization of stable ruthenabenzenes starting from HCCCH(OH)CCH

The acid treatment of a ruthenabenzene yielded an unusual dialdehyde. Interestingly, this dialdehyde has notable anti-oxidative properties and resists even nitric acid. This stability is confirmed by chemical and electrochemical experiments. In addition, a stable cyclic anhydride is synthesized from the dialdehyde via an environmentally friendly electrochemical method.

Synthesis and characterization of a novel dialdehyde and cyclic anhydride

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Synthesis and characterization of stable ruthenabenzenes starting from HCCCH(OH)CCH

Synthesis and characterization of a novel dialdehyde and cyclic anhydride