Iridium‐Catalyzed Reductive Carbon–Carbon Bond Cleavage Reaction on a Curved Pyridylcorannulene Skeleton

Shohei Tashiro, Mihoko Yamada, Mitsuhiko Shionoya

doi:10.1002/ange.201500819

Iridium‐Catalyzed Reductive Carbon–Carbon Bond Cleavage Reaction on a Curved Pyridylcorannulene Skeleton

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<jats:title>Abstract</jats:title><jats:p>The cleavage of CC bonds in π‐conjugated systems is an important method for controlling their shape and coplanarity. An efficient way for the cleavage of an aromatic CC bond in a typical buckybowl corannulene skeleton is reported. The reaction of 2‐pyridylcorannulene with a catalytic amount of IrCl<jats:sub>3</jats:sub>⋅<jats:italic>n</jats:italic> H<jats:sub>2</jats:sub>O in ethylene glycol at 250 °C resulted in a structural transformation from the curved corannulene skeleton to a strain‐free flat benzo[<jats:italic>ghi</jats:italic>]fluoranthene skeleton through a site‐selective CC cleavage reaction. This cleavage reaction was found to be driven by both the coordination of the 2‐pyridyl substituent to iridium and the relief of strain in the curved corannulene skeleton. This finding should facilitate the design of carbon nanomaterials based on CC bond cleavage reactions.</jats:p>