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Article: Intramolecular C-H insertion vs. Friedel-Crafts coupling induced by silyl cation-promoted C-F activation

TitleIntramolecular C-H insertion vs. Friedel-Crafts coupling induced by silyl cation-promoted C-F activation
Authors
Allemann, OliverBaldridge, Kim K.Siegel, Jay S.
Issue Date2015
Citation
Organic Chemistry Frontiers, 2015, v. 2, n. 9, p. 1018-1021 How to Cite?
DOI: http://dx.doi.org/10.1039/c5qo00170f
AbstractSilyl cation-promoted aryl C-F activation can lead to formal C-H activation and the formation of new C(ar)-C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C-H bond. From competition experiments, a relation between reaction rate and C-H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.
Persistent Identifierhttp://hdl.handle.net/10722/341174
ISSN
2052-4110
2023 SCImago Journal Rankings: 1.016
ISI Accession Number ID
WOS:000364449800003

 

DC FieldValueLanguage
dc.contributor.authorAllemann, Oliver-
dc.contributor.authorBaldridge, Kim K.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:40:45Z-
dc.date.available2024-03-13T08:40:45Z-
dc.date.issued2015-
dc.identifier.citationOrganic Chemistry Frontiers, 2015, v. 2, n. 9, p. 1018-1021-
dc.identifier.issn2052-4110-
dc.identifier.urihttp://hdl.handle.net/10722/341174-
dc.description.abstractSilyl cation-promoted aryl C-F activation can lead to formal C-H activation and the formation of new C(ar)-C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C-H bond. From competition experiments, a relation between reaction rate and C-H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.-
dc.languageeng-
dc.relation.ispartofOrganic Chemistry Frontiers-
dc.titleIntramolecular C-H insertion vs. Friedel-Crafts coupling induced by silyl cation-promoted C-F activation-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c5qo00170f-
dc.identifier.scopuseid_2-s2.0-84939518497-
dc.identifier.volume2-
dc.identifier.issue9-
dc.identifier.spage1018-
dc.identifier.epage1021-
dc.identifier.eissn2052-4129-
dc.identifier.isiWOS:000364449800003-

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