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Iridium‐Catalyzed Reductive Carbon–Carbon Bond Cleavage Reaction on a Curved Pyridylcorannulene Skeleton
Author(s) -
Tashiro Shohei,
Yamada Mihoko,
Shionoya Mitsuhiko
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500819
Subject(s) - corannulene , chemistry , bond cleavage , catalysis , conjugated system , cleavage (geology) , photochemistry , fullerene , organic chemistry , materials science , polymer , fracture (geology) , composite material
The cleavage of CC bonds in π‐conjugated systems is an important method for controlling their shape and coplanarity. An efficient way for the cleavage of an aromatic CC bond in a typical buckybowl corannulene skeleton is reported. The reaction of 2‐pyridylcorannulene with a catalytic amount of IrCl 3 ⋅ n H 2 O in ethylene glycol at 250 °C resulted in a structural transformation from the curved corannulene skeleton to a strain‐free flat benzo[ ghi ]fluoranthene skeleton through a site‐selective CC 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 CC bond cleavage reactions.