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Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes.

07:00 EST 13th February 2020 | BioPortfolio

Summary of "Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes."

On treatment with the catalyst, InBr 3 , 1,1-difluoroallenes that bear a cyclopentene moiety and an aryl group underwent domino ring assembly in the presence or absence of N -bromosuccinimide or N -iodosuccinimide to afford aryne precursors such as three-ringed ortho -fluoro(halo)phenanthrenes, four-ringed ortho -fluoro(halo)tetraphenes, ortho -fluoro(halo)chrysenes and fluoro[4]helicenes. Metalation of the aryne precursors followed by elimination of the fluoride resulted in the unprecedented systematic generation of arynes bearing π-extended systems. Diels-Alder reactions of these arynes with isobenzofurans afforded the corresponding cycloadducts whose reductive aromatisation in an SnCl 2 /HBr system furnished fully aromatised benzotriphenylenes. In addition, oxidative aryl-aryl coupling (the Scholl reaction) of these benzotriphenylenes facilitated the synthesis of 'half HBCs' (hexabenzocoronenes).

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Name: Chemistry, an Asian journal
ISSN: 1861-471X
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