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분자활성촉매반응연구단
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Scope and Mechanistic Studies on the Ruthenium-Catalyzed Multicomponent Deaminative C-H Coupling Reaction of Phenols with Aldehydes and Enamines for the Formation of Xanthene and Dioxacyclic Derivatives

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dc.contributor.authorPannilawithana, Nuwan-
dc.contributor.authorMina Son-
dc.contributor.authorDonghun Hwang-
dc.contributor.authorMu-Hyun Baik-
dc.contributor.authorYi, Chae S.-
dc.date.accessioned2023-08-02T22:00:28Z-
dc.date.available2023-08-02T22:00:28Z-
dc.date.created2023-07-17-
dc.date.issued2023-06-
dc.identifier.issn2155-5435-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/13680-
dc.description.abstractThe in situ generated catalytic systemfrom thetetranuclear Ru-H complex [(PCy3)(CO)RuH](4)(O)(OH)(2) (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone(L1) has been found to mediate a multicomponent deaminativecoupling reaction of phenols with aldehydes and enamines to form xantheneproducts. The multicomponent C-H coupling reaction of phenolswith 2-hydroxybenzaldehydes and cyclic enamines efficiently installedthe tricyclic 1,3-dioxacin derivatives, while the analogous couplingreaction of phenols with 2-hydroxybenzaldehydes and triethylamineselectively formed bicyclic 1,5-dioxacyclic derivatives. The densityfunctional theory (DFT) calculations established two energeticallyviable mechanistic pathways for the formation of xanthene products,in which both pathways identified the C-O bond cleavage stepas the turnover limiting step. A Hammett plot from the coupling reactionof 3,5-dimethoxyphenol with an enamine and para-substitutedbenzaldehydes p-X-C6H4CHO (X= OMe, Me, H, Cl, CF3) showed a negative slope (& rho;= -0.98). The calculated energy analysis showed a similar trend(& rho; = -0.59) for the mechanism via the C-O cleavagerate-limiting step. The combined experimental and DFT computationalresults support a mechanistic path that involves the dehydrative C-Hcoupling of phenol with aldehyde, followed by the deaminative couplingreaction with an enamine in forming the xanthene product.-
dc.language영어-
dc.publisherAMER CHEMICAL SOC-
dc.titleScope and Mechanistic Studies on the Ruthenium-Catalyzed Multicomponent Deaminative C-H Coupling Reaction of Phenols with Aldehydes and Enamines for the Formation of Xanthene and Dioxacyclic Derivatives-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid001016122300001-
dc.identifier.scopusid2-s2.0-85164420994-
dc.identifier.rimsid81182-
dc.contributor.affiliatedAuthorMina Son-
dc.contributor.affiliatedAuthorDonghun Hwang-
dc.contributor.affiliatedAuthorMu-Hyun Baik-
dc.identifier.doi10.1021/acscatal.3c01651-
dc.identifier.bibliographicCitationACS CATALYSIS, v.13, no.13, pp.9051 - 9063-
dc.relation.isPartOfACS CATALYSIS-
dc.citation.titleACS CATALYSIS-
dc.citation.volume13-
dc.citation.number13-
dc.citation.startPage9051-
dc.citation.endPage9063-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryChemistry, Physical-
dc.subject.keywordPlusMOLECULAR-ORBITAL METHODS-
dc.subject.keywordPlusEFFECTIVE CORE POTENTIALS-
dc.subject.keywordPlusBOND ACTIVATION-
dc.subject.keywordPlusALKYLATION-
dc.subject.keywordPlusCLEAVAGE-
dc.subject.keywordPlusAMINES-
dc.subject.keywordPlusSALTS-
dc.subject.keywordAuthormulticomponent reaction-
dc.subject.keywordAuthordeaminative coupling-
dc.subject.keywordAuthorruthenium catalyst-
dc.subject.keywordAuthorxanthene-
dc.subject.keywordAuthordioxacin-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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