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C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue

Huang, Lin; Qiu, Mengyu; Chang, Zhihao; Browne, Duncan L; Huang, Jianhui; (2024) C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue. Organic Chemistry Frontiers 10.1039/d4qo00415a. (In press).

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Abstract

A novel piperazine-embedded azadibenzo[a,g]corannulene analogue was synthesized by a four-step bottom-up synthesis, including a nucleophilic aromatic substitution (SNAr) and a palladium-catalyzed intramolecular C–H activation arylation as key steps. This intriguing molecule represents the first example of an azacorannulene analogue bearing a piperazine ring on its polycyclic skeleton. X-ray diffraction analysis reveals a Cs-symmetric deformed bowl-shaped structure and one-dimensional columnar packing through π–π interactions with slightly offset centres, attributed to the presence of two sp3 carbons on its polycyclic core.

Type: Article
Title: C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue
DOI: 10.1039/d4qo00415a
Publisher version: https://doi.org/10.1039/d4qo00415a
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10192733
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