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Reversible, Room-Temperature CC Bond Activation of Benzene by an Isolable Metal Complex

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posted on 2019-06-28, 00:00 authored by Jamie Hicks, Petra Vasko, Jose M. Goicoechea, Simon Aldridge
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.