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Article: Palladium-catalyzed redox cascade for direct β-arylation of ketones

TitlePalladium-catalyzed redox cascade for direct β-arylation of ketones
Authors
KeywordsConjugate addition
Ketone dehydrogenation
Palladium-catalyzed redox cascade methods
Redox-neutral catalysis
β-Arylation of ketones
Aryl-X bond activation
Issue Date2018
Citation
Tetrahedron, 2018, v. 74, n. 26, p. 3253-3265 How to Cite?
Abstract© 2018 Elsevier Ltd Herein we report a full article about the detailed design and development of two palladium-catalyzed redox cascade methods that enable direct β-arylation of ketones. Palladium-catalyzed ketone dehydrogenation, aryl-X bond activation and conjugate addition were merged into a redox-neutral catalytic cycle. Non-metal-based aryl electrophiles were used as both the oxidant and the aryl source. The β-arylation with aryl iodides was achieved site-selectively with Pd(TFA)2/P(i-Pr)3 as the precatalyst and AgTFA as the iodide scavenger. Both cyclic and linear ketones can react to give β-aryl ketones with excellent functional group tolerance. The β-arylation with diaryliodonium salts was realized without stoichiometric heavy metal additives, and proved to be redox-neutral. A wider substrate scope regarding aryl groups and ketones was obtained for the arylation with diaryliodonium salts, and the possible involvement of palladium nanoparticles as the active catalyst was examined and discussed.
Persistent Identifierhttp://hdl.handle.net/10722/276589
ISSN
2017 Impact Factor: 2.377
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorHuang, Zhongxing-
dc.contributor.authorDong, Guangbin-
dc.date.accessioned2019-09-18T08:34:04Z-
dc.date.available2019-09-18T08:34:04Z-
dc.date.issued2018-
dc.identifier.citationTetrahedron, 2018, v. 74, n. 26, p. 3253-3265-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10722/276589-
dc.description.abstract© 2018 Elsevier Ltd Herein we report a full article about the detailed design and development of two palladium-catalyzed redox cascade methods that enable direct β-arylation of ketones. Palladium-catalyzed ketone dehydrogenation, aryl-X bond activation and conjugate addition were merged into a redox-neutral catalytic cycle. Non-metal-based aryl electrophiles were used as both the oxidant and the aryl source. The β-arylation with aryl iodides was achieved site-selectively with Pd(TFA)2/P(i-Pr)3 as the precatalyst and AgTFA as the iodide scavenger. Both cyclic and linear ketones can react to give β-aryl ketones with excellent functional group tolerance. The β-arylation with diaryliodonium salts was realized without stoichiometric heavy metal additives, and proved to be redox-neutral. A wider substrate scope regarding aryl groups and ketones was obtained for the arylation with diaryliodonium salts, and the possible involvement of palladium nanoparticles as the active catalyst was examined and discussed.-
dc.languageeng-
dc.relation.ispartofTetrahedron-
dc.subjectConjugate addition-
dc.subjectKetone dehydrogenation-
dc.subjectPalladium-catalyzed redox cascade methods-
dc.subjectRedox-neutral catalysis-
dc.subjectβ-Arylation of ketones-
dc.subjectAryl-X bond activation-
dc.titlePalladium-catalyzed redox cascade for direct β-arylation of ketones-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.tet.2018.03.017-
dc.identifier.scopuseid_2-s2.0-85046106175-
dc.identifier.volume74-
dc.identifier.issue26-
dc.identifier.spage3253-
dc.identifier.epage3265-
dc.identifier.eissn1464-5416-
dc.identifier.isiWOS:000436222800008-

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