Reversible, room-temperature C—C bond activation of benzene by an isolable metal complex

The activation of C-C bonds is of fundamental interest in the construction of complex molecules from petrochemical feedstocks. In the case of the archetypal aromatic hydrocarbon benzene, C-C cleavage is thermodynamically disfavored, and is brought about only by transient highly reactive species gene...

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Bibliographic Details
Main Authors: Hicks, J, Vasko, P, Goicoechea, J, Aldridge, S
Format: Journal article
Language:English
Published: American Chemical Society 2019
Description
Summary:The activation of C-C bonds is of fundamental interest in the construction of complex molecules from petrochemical feedstocks. In the case of the archetypal aromatic hydrocarbon benzene, C-C cleavage is thermodynamically disfavored, and is brought about only by transient highly reactive species generated in situ. Here we show that the oxidative addition of the C-C bond in benzene by an isolated metal complex is not only possible, but occurs at room temperature and reversibly at a single aluminium center in [(NON)Al]- (where NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethylxanthene). Selectivity over C-H bond activation is achieved kinetically and allows for the generation of functionalized acyclic products from benzene.