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Symmetrical and unsymmetrical fluorine-rich ullazines via controlled cycloaromatizations

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Abstract

We report the synthesis of a series of fluorine-rich ullazines via well-controlled cycloaromatizations of highly electron-deficient alkynes. Specifically, three symmetrically-functionalized and three unsymmetrically-functionalized ullazine cores were constructed from 1-(2,6-dialkynylphenyl)-1H-pyrroles via controlled electrophilic cyclizations of highly electron-poor pentafluorosulfanylated (i.e., SF5-containing) phenylethynyl moieties onto the pyrrole. While the diminished reactivity of the electron-poor alkynes was initially problematic, this feature was subsequently found to be pivotal in facilitating thermal control of mono- versus double 6-endo-trig ring-closure in the key step. Iodinated ullazine products were shown to undergo further facile transformation into more complex unsymmetrical targets. The synthetic strategies reported herein grant access to a host of symmetrically- and unsymmetrically-decorated fluorine-rich ullazines with potential value as light-harvesting materials (e.g., dye-sensitized solar cells, organic photovoltaics) or as advanced intermediates for further synthetic elaboration.

Graphical abstract: Symmetrical and unsymmetrical fluorine-rich ullazines via controlled cycloaromatizations

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Article information


Submitted
08 Jan 2020
Accepted
28 Jan 2020
First published
05 Feb 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Symmetrical and unsymmetrical fluorine-rich ullazines via controlled cycloaromatizations

G. Zhang, P. Gautam and J. M. W. Chan, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00033G

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