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Building a Parent Iridabenzene Structure from Acetylene and Dichloromethane on an Iridium Center

IIQ

Metallabenzenes are interesting species which have attracted ample interest from the academic community because their structures, electronic properties and reactivity. Despite recent significant advances in this field, which have been reviewed lately, and thedevelopment of different synthetic methods, a “parent” metallabenzene, that is, a complexcomprising only CH units in the aromatic six-membered ring, remains an unknown andappealing target. In this communication we have described the formation of the first parent metallabenzeneon the reaction of the bis(ethylene) complex [TpIr(C2H4)2] (Tp =hydrotris(pyrazolyl)borate) with acetylene in dichloromethane. Iridabenzene formation is proposed to be the result of the coupling of an iridacyclopentadiene, in turn formed from two acetylene molecules at the Ir centre, and the dichloromethane-derived chlorocarbene“:C(H)Cl” followed by an alfa-Cl elimination event. Additional interesting reactivity has been disclosed in the presence of co-solvents such as Et2O or THF.

Los metalabencenos son especies de gran interés para la comunidad científica debido a sus estructuras, propiedades electrónicas y reactividad. Aunque se han obtenido resultados importantes en este campo y se siguen desarrollando diferentes métodos de síntesis, hasta la aparición de nuestro trabajo no se había descrito un metalabenceno sin sustituyentes. En esta comunicación se describe la síntesis del primer metalabenceno no sustituido a partir de la reacción del complejo de bisetileno [TpIr(C2H4)2] (Tp =hidrotris(pirazolil)borato) con acetileno en diclorometano. La formación del iridabencenose propone como el resultado de la reacción de un iridaciclopenteno, formado mediante el acoplamiento de dos moléculas de acetileno en el centro metálico, y el clorocarbenoderivado del diclorometano “:C(H)Cl”, seguido de una eliminación alfa-Cl. Se presentan también resultados interesantes cuando la reacción se lleva a cabo en presencia de Et2O oTHF.

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