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Article: 1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls

Title1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls
Authors
Liu, ShiRoch, Loïc M.Allemann, OliverXu, JunVanthuyne, NicolasBaldridge, Kim K.Siegel, Jay S.
Issue Date2018
Citation
Journal of Organic Chemistry, 2018, v. 83, n. 7, p. 3979-3986 How to Cite?
DOI: http://dx.doi.org/10.1021/acs.joc.8b00320
AbstractAnnulated corannulenes 3-5 form via distinct synthetic pathways: (i) Pd-catalyzed sp3 CH insertion, (ii) Pd-catalyzed aryl coupling, and (iii) silyl cation-promoted C-F activation/CH insertion. Crystal structure, redox, and photophysical studies elucidate the differing influence of 1,2,3- versus 1,2-indeno ring fusions. Mono and dianions of 3-5 are characterized. Resolution of 4 gives enantiopure forms, allowing assessment of the bowl-inversion barrier.
Persistent Identifierhttp://hdl.handle.net/10722/341225
ISSN
0022-3263
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID
WOS:000429886100055

 

DC FieldValueLanguage
dc.contributor.authorLiu, Shi-
dc.contributor.authorRoch, Loïc M.-
dc.contributor.authorAllemann, Oliver-
dc.contributor.authorXu, Jun-
dc.contributor.authorVanthuyne, Nicolas-
dc.contributor.authorBaldridge, Kim K.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:41:09Z-
dc.date.available2024-03-13T08:41:09Z-
dc.date.issued2018-
dc.identifier.citationJournal of Organic Chemistry, 2018, v. 83, n. 7, p. 3979-3986-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/341225-
dc.description.abstractAnnulated corannulenes 3-5 form via distinct synthetic pathways: (i) Pd-catalyzed sp3 CH insertion, (ii) Pd-catalyzed aryl coupling, and (iii) silyl cation-promoted C-F activation/CH insertion. Crystal structure, redox, and photophysical studies elucidate the differing influence of 1,2,3- versus 1,2-indeno ring fusions. Mono and dianions of 3-5 are characterized. Resolution of 4 gives enantiopure forms, allowing assessment of the bowl-inversion barrier.-
dc.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.title1,2,3- versus 1,2-Indeno Ring Fusions Influence Structure Property and Chirality of Corannulene Bowls-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.joc.8b00320-
dc.identifier.pmid29577722-
dc.identifier.scopuseid_2-s2.0-85045085121-
dc.identifier.volume83-
dc.identifier.issue7-
dc.identifier.spage3979-
dc.identifier.epage3986-
dc.identifier.eissn1520-6904-
dc.identifier.isiWOS:000429886100055-

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