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분자활성촉매반응연구단
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Unraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C―H Functionalization via the Spin-Center Shift

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dc.contributor.authorWonjun Choi-
dc.contributor.authorLeejae Kim-
dc.contributor.authorSungwoo Hong-
dc.date.accessioned2024-05-27T05:30:03Z-
dc.date.available2024-05-27T05:30:03Z-
dc.date.created2024-03-25-
dc.date.issued2024-05-
dc.identifier.issn2198-3844-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/15187-
dc.description.abstractDespite the simplicity and abundance of ethylene, its practical application presents significant hurdles due to its nature as a highly flammable gas. Herein, a strategic use of easily handled vinyl ether is reported as a latent ethylene surrogate achieved via a spin-center shift (SCS) pathway, enabling the successful three-component reaction that bridges heteroarenes and various coupling partners, including sulfinates, thiols, and phosphine oxides. Through a photoredox catalytic process, alpha-oxy radicals are generated by combining various radicals with phenyl vinyl ether, which are subsequently added to N-heteroarenes. Subsequently, the radical-mediated SCS pathway serves as the driving force for CO bond cleavage, effectively engaging the phenoxy group as a leaving group. In addition, by broadening the utility of the method, a valuable synthon is provided for efficient CH vinylation of N-heteroarenes following sulfonyl group elimination. This approach not only enriches the toolbox of synthetic methodology but also provides a more streamlined alternative, circumventing the challenges associated with direct ethylene gas usage. The versatility of the method, particularly evident in late-stage functionalizations of medicinally relevant molecules and peptides, underscores its capability to produce invaluable three-component compounds and vinylated N-heteroarene derivatives.-
dc.language영어-
dc.publisherWiley-VCH Verlag-
dc.titleUnraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C―H Functionalization via the Spin-Center Shift-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid001183798300001-
dc.identifier.scopusid2-s2.0-85187496101-
dc.identifier.rimsid82805-
dc.contributor.affiliatedAuthorWonjun Choi-
dc.contributor.affiliatedAuthorLeejae Kim-
dc.contributor.affiliatedAuthorSungwoo Hong-
dc.identifier.doi10.1002/advs.202309800-
dc.identifier.bibliographicCitationAdvanced Science, v.11, no.19-
dc.relation.isPartOfAdvanced Science-
dc.citation.titleAdvanced Science-
dc.citation.volume11-
dc.citation.number19-
dc.description.journalClass1-
dc.description.journalClass1-
dc.description.isOpenAccessY-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalWebOfScienceCategoryChemistry, Multidisciplinary-
dc.relation.journalWebOfScienceCategoryNanoscience & Nanotechnology-
dc.relation.journalWebOfScienceCategoryMaterials Science, Multidisciplinary-
dc.subject.keywordPlusMETAL-FREE-
dc.subject.keywordPlusRADICALS-
dc.subject.keywordPlusTETRAFLUOROETHYLENE-
dc.subject.keywordPlusDIFUNCTIONALIZATION-
dc.subject.keywordPlusGENERATION-
dc.subject.keywordPlusALDEHYDES-
dc.subject.keywordPlusALKENES-
dc.subject.keywordPlusKETONES-
dc.subject.keywordAuthorCH vinylation-
dc.subject.keywordAuthorethylene surrogate-
dc.subject.keywordAuthorspin-center shift (SCS)-
dc.subject.keywordAuthorvinyl ether-
dc.subject.keywordAuthoralpha-oxy radical-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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