Iridium-catalyzed reductive carbon-carbon bond cleavage reaction on a curved pyridylcorannulene skeleton

Angewandte Chemie
Shohei TashiroMitsuhiko Shionoya

Abstract

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 IrCl3 ⋅n H2 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 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.

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Citations

Feb 12, 2019·Chemistry : a European Journal·Friederike RatschHans-Günther Schmalz
May 6, 2019·Chemistry, an Asian Journal·Martin Jakoobi, Alexey G Sergeev
Aug 6, 2015·Acta Crystallographica. Section C, Structural Chemistry·Sarah N SpisakMarina A Petrukhina
Dec 15, 2020·Chemistry : a European Journal·Friederike RatschHans-Günther Schmalz
May 28, 2021·Chemical Science·Gabrielle A LeithNatalia B Shustova
Mar 19, 2019·Journal of the American Chemical Society·Martin JakoobiAlexey G Sergeev
Feb 23, 2019·Journal of the American Chemical Society·Xuelin YaoKlaus Müllen

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