6533b861fe1ef96bd12c448c

RESEARCH PRODUCT

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

Petra VaskoPetra VaskoSimon AldridgeJamie HicksJose M. Goicoechea

subject

chemistry.chemical_classificationchemistry.chemical_elementGeneral Chemistry010402 general chemistryCleavage (embryo)Photochemistry01 natural sciencesBiochemistryOxidative additionCatalysis3. Good health0104 chemical sciencesMetalchemistry.chemical_compoundColloid and Surface ChemistrychemistryAluminiumvisual_artvisual_art.visual_art_mediumMoleculeBenzeneSelectivityAromatic hydrocarbon

description

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.

10.1021/jacs.9b05925https://doi.org/10.1021/jacs.9b05925