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분자활성촉매반응연구단
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Experimental and Computational Studies on the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Aldehydes for the Synthesis of 2-Alkylphenol, Benzofuran, and Xanthene Derivatives

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dc.contributor.authorPannilawithana, Nuwan-
dc.contributor.authorBimal Pudasaini-
dc.contributor.authorMu-Hyun Baik-
dc.contributor.authorYi, Chae S.-
dc.date.accessioned2021-10-07T05:30:04Z-
dc.date.available2021-10-07T05:30:04Z-
dc.date.created2021-09-27-
dc.date.issued2021-08-25-
dc.identifier.issn0002-7863-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/10353-
dc.description.abstract© 2021 American Chemical Society.The cationic Ru-H complex [(C6H6)(PCy3)(CO)RuH]+BF4- (1) was found to be an effective catalyst for the dehydrative C-H coupling reaction of phenols and aldehydes to form 2-alkylphenol products. The coupling reaction of phenols with branched aldehydes selectively formed 1,1-disubstituted benzofurans, while the coupling reaction with salicylaldehydes yielded xanthene derivatives. A normal deuterium isotope effect was observed from the coupling reaction of 3-methoxyphenol with benzaldehyde and 2-propanol/2-propanol-d8 (kH/kD = 2.3 ± 0.3). The carbon isotope effect was observed on the benzylic carbon of the alkylation product from the coupling reaction of 3-methoxyphenol with 4-methoxybenzaldehyde (C(3) 1.021(3)) and on both benzylic and ortho-arene carbons from the coupling reaction with 4-trifluorobenzaldehdye (C(2) 1.017(3), C(3) 1.011(2)). The Hammett plot from the coupling reaction of 3-methoxyphenol with para-substituted benzaldehydes p-X-C6H4CHO (X = OMe, Me, H, F, Cl, CF3) displayed a V-shaped linear slope. Catalytically relevant Ru-H complexes were observed by NMR from a stoichiometric reaction mixture of 1, 3-methoxyphenol, benzaldehyde, and 2-propanol in CD2Cl2. The DFT calculations provided a detailed catalysis mechanism featuring an electrophilic aromatic substitution of the aldehyde followed by the hydrogenolysis of the hydroxy group. The calculations also revealed a mechanistic rationale for the strong electronic effect of the benzaldehdye substrates p-X-C6H4CHO (X = OMe, CF3) in controlling the turnover-limiting step. The catalytic C-H coupling method provides an efficient synthetic protocol for 2-alkylphenols, 1,1-disubstituted benzofurans, and xanthene derivatives without employing any reactive reagents or forming wasteful byproducts.-
dc.language영어-
dc.publisherAmerican Chemical Society-
dc.titleExperimental and Computational Studies on the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Aldehydes for the Synthesis of 2-Alkylphenol, Benzofuran, and Xanthene Derivatives-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid000691789500062-
dc.identifier.scopusid2-s2.0-85114170941-
dc.identifier.rimsid76395-
dc.contributor.affiliatedAuthorBimal Pudasaini-
dc.contributor.affiliatedAuthorMu-Hyun Baik-
dc.identifier.doi10.1021/jacs.1c06887-
dc.identifier.bibliographicCitationJournal of the American Chemical Society, v.143, no.33, pp.13428 - 13440-
dc.relation.isPartOfJournal of the American Chemical Society-
dc.citation.titleJournal of the American Chemical Society-
dc.citation.volume143-
dc.citation.number33-
dc.citation.startPage13428-
dc.citation.endPage13440-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryChemistry, Multidisciplinary-
dc.subject.keywordPlusEFFECTIVE CORE POTENTIALS-
dc.subject.keywordPlusMOLECULAR-ORBITAL METHODS-
dc.subject.keywordPlusALPHA-ALKYLATION-
dc.subject.keywordPlusACTIVATION-
dc.subject.keywordPlusKETONES-
dc.subject.keywordPlusALCOHOLS-
dc.subject.keywordPlusOLEFINS-
dc.subject.keywordPlusBONDS-
dc.subject.keywordPlusATOM-
dc.subject.keywordPlusFUNCTIONALIZATION-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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