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Article: Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: A stoichiometric heavy metal-free and user-friendly approach

TitlePalladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: A stoichiometric heavy metal-free and user-friendly approach
Authors
Issue Date2015
Citation
Chemical Science, 2015, v. 6, n. 10, p. 5491-5498 How to Cite?
Abstract© The Royal Society of Chemistry 2015. We herein report a new protocol for the Pd-catalyzed β-arylation of ketones without stoichiometric heavy metals. Widely accessible diaryliodonium salts are used as both the oxidant and aryl source. This tandem redox catalysis merges ketone dehydrogenation and conjugate addition without an additional oxidant or reductant. This transformation features the use of a unique bis-N-tosylsulfilimine ligand and the combination of potassium trifluoroacetate/trifluoroacetic acid to maintain an appropriate acidity of the reaction medium. The reaction tolerates both air and moisture, and shows a broad substrate scope. Kinetics studies, along with filtration and poisoning tests, support the involvement of palladium nanoparticles in the catalysis.
Persistent Identifierhttp://hdl.handle.net/10722/276696
ISSN
2017 Impact Factor: 9.063
2015 SCImago Journal Rankings: 4.974
PubMed Central ID
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorHuang, Zhongxing-
dc.contributor.authorSam, Quynh P.-
dc.contributor.authorDong, Guangbin-
dc.date.accessioned2019-09-18T08:34:23Z-
dc.date.available2019-09-18T08:34:23Z-
dc.date.issued2015-
dc.identifier.citationChemical Science, 2015, v. 6, n. 10, p. 5491-5498-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10722/276696-
dc.description.abstract© The Royal Society of Chemistry 2015. We herein report a new protocol for the Pd-catalyzed β-arylation of ketones without stoichiometric heavy metals. Widely accessible diaryliodonium salts are used as both the oxidant and aryl source. This tandem redox catalysis merges ketone dehydrogenation and conjugate addition without an additional oxidant or reductant. This transformation features the use of a unique bis-N-tosylsulfilimine ligand and the combination of potassium trifluoroacetate/trifluoroacetic acid to maintain an appropriate acidity of the reaction medium. The reaction tolerates both air and moisture, and shows a broad substrate scope. Kinetics studies, along with filtration and poisoning tests, support the involvement of palladium nanoparticles in the catalysis.-
dc.languageeng-
dc.relation.ispartofChemical Science-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.titlePalladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: A stoichiometric heavy metal-free and user-friendly approach-
dc.typeArticle-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1039/c5sc01636c-
dc.identifier.pmid29861889-
dc.identifier.pmcidPMC5949602-
dc.identifier.scopuseid_2-s2.0-84941702205-
dc.identifier.volume6-
dc.identifier.issue10-
dc.identifier.spage5491-
dc.identifier.epage5498-
dc.identifier.eissn2041-6539-
dc.identifier.isiWOS:000361212000016-

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