Reversible, room-temperature C-C bond activation of benzene by an isolable metal complex
Hicks, Jamie; Vasko, Petra; Goicoechea, Jose Manuel; Aldridge, Simon (2019). Reversible, room-temperature C-C bond activation of benzene by an isolable metal complex. Journal of the American Chemical Society, 141 (28), 11000-11003. DOI: 10.1021/jacs.9b05925
Published inJournal of the American Chemical Society
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© 2019 American Chemical Society
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 disfavoured, 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 centre 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.