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Title: Bilateral aromatic extension of corannulene nucleus
Authors: Halilovic, Dzeneta
Csókás, Dániel
Webster, Richard David
Stuparu, Mihaiela Corina
Keywords: Science::Chemistry
Issue Date: 2022
Source: Halilovic, D., Csókás, D., Webster, R. D. & Stuparu, M. C. (2022). Bilateral aromatic extension of corannulene nucleus. European Journal of Organic Chemistry, 2022(18), e202101548-.
Project: 2018-T1-001-176
Journal: European Journal of Organic Chemistry
Abstract: Herein we show that a dibromo imide derivative of corannulene could be subjected to a palladium-catalyzed Heck reaction in order to install aryl vinylene groups in a bilateral fashion on the C5-symmetric aromatic nucleus. A photochemically-induced oxidative cyclization then affords π-extended structures in isolated overall yields of 35–44 %. Due to the aromatic area extension and the presence of electron withdrawing groups, the synthesized molecules exhibit an anodic shift of ≈1 V in their first reduction potential as compared to pristine corannulene. The bilateral growth of the aromatic scaffold, therefore, represents a viable strategy to prepare π-extended corannulenes with an electron deficient character.
ISSN: 1434-193X
DOI: 10.1002/ejoc.202101548
Rights: © 2022 Wiley-VCH GmbH. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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