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

Abstract

The cleavage of C À Cbonds in p-conjugated systems is an important method for controlling their shape and coplanarity.A ne fficient way for the cleavage of an aromatic CÀCb ond in at ypical buckybowl corannulene skeleton is reported. The reaction of 2-pyridylcorannulene with acatalytic amount of IrCl 3 ·n H 2 Oi ne thylene glycol at 250 8 8Cr esulted in as tructural transformation from the curved corannulene skeleton to as train-free flat benzo[ghi]fluoranthene skeleton through as ite-selective CÀCc leavage 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 À Cb ond cleavage reactions.will enabled the development of unique and efficient methods for the chemical modification of non-planar carbon nanomaterials.

Regioselective Hydrogenation of a 60-Carbon Nanographene Molecule toward a Circumbiphenyl Core

“…9 More recently, Shionoya et al described a catalytic reductive C−C bond cleavage of a corannulene derivative, leading to a benzo[ghi]fluoranthene structure. 10 On the other hand, "π-truncation" of aromatic structures has been applied to fullerene, with the formation of a hoop-shaped cyclic benzenoid compound by Nakamura et al as one of the most elegant examples. 11 Nevertheless, compared with the πexpansion procedure, the "π-truncation" strategy is underdeveloped.…”