Reactivity and Applications of α-Metalated Ylides

Part of the Structure and Bonding book series (STRUCTURE, volume 177)


α-Metalated ylides, the so-called yldiides, represent a unique class of carbon-centered donor ligands. With two lone pairs of electrons at the central ylidic carbon atom, they are closely related to important organometallic ligand systems, above all bisylides and methandiides, and thus have attracted considerable research interest both from experimental and theoretical points of view. Although the number of isolated and structurally characterized yldiides is still limited, reactivity studies have demonstrated their exciting chemistry. Nowadays applications range from their use as powerful, highly nucleophilic reagents in organic synthesis such as in cascade reactions to their use as strong σ- and π-donor ligands in main group element and transition metal chemistry. The unique reactivity and donor capacity of α-metalated ylides is thereby strongly connected with the availability of the two lone pairs at the ylidic carbon atom, which makes yldiides to a special class of ylidic compounds. This review summarizes the chemistry of yldiides, particularly highlighting recent developments in their isolation and applications, also emphasizing structural and electronic properties of these compounds.


Carbanions Catalysis Coordination chemistry Electronic structure Ylide chemistry 


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Authors and Affiliations

  1. 1.Lehrstuhl für Anorganische Chemie IIFakultät für Chemie und BiochemieBochumGermany

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