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분자활성 촉매반응 연구단
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Endo-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization

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dc.contributor.authorHoonchul Choi-
dc.contributor.authorXiang Lyu-
dc.contributor.authorDongwook Kim-
dc.contributor.authorSangwon Seo-
dc.contributor.authorSukbok Chang-
dc.date.accessioned2022-07-29T07:44:42Z-
dc.date.available2022-07-29T07:44:42Z-
dc.date.created2022-06-27-
dc.date.issued2022-06-
dc.identifier.issn0002-7863-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/12036-
dc.description.abstract© Intramolecular alkyne hydroamidation represents a straightforward approach for the access to synthetically valuable cyclic enamides. Despite some advances made in this realm, the ability to attain a precise regiocontrol still remains challenging, especially for endo cyclization that leads to six-membered and larger azacyclic rings. Herein, we report a NiH-catalyzed intramolecular hydroamidation of alkynyl dioxazolones that allows for an excellent endo selectivity, thus affording a range of six- to eight-membered endocyclic enamides with a broad scope. Mechanistic investigations revealed that Ni(I) catalysis is operative in the current system, proceeding via regioselective syn-hydronickelation, alkenylnickel E/Z isomerization, and Ni-centered inner-sphere nitrenoid transfer. In particular, the key alkenylnickel isomerization step, which previously lacked mechanistic understandings, was found to take place through the η2-vinyl transition state. The synthetic value of this protocol was demonstrated by diastereoselective modifications of the obtained endocyclic enamides to highly functionalized δ-lactam scaffolds.-
dc.language영어-
dc.publisherAmerican Chemical Society-
dc.titleEndo-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization-
dc.typeArticle-
dc.type.rimsART-
dc.identifier.wosid000810029900001-
dc.identifier.scopusid2-s2.0-85131771540-
dc.identifier.rimsid78378-
dc.contributor.affiliatedAuthorHoonchul Choi-
dc.contributor.affiliatedAuthorXiang Lyu-
dc.contributor.affiliatedAuthorDongwook Kim-
dc.contributor.affiliatedAuthorSangwon Seo-
dc.contributor.affiliatedAuthorSukbok Chang-
dc.identifier.doi10.1021/jacs.2c03777-
dc.identifier.bibliographicCitationJournal of the American Chemical Society, v.144, no.22, pp.10064 - 10074-
dc.relation.isPartOfJournal of the American Chemical Society-
dc.citation.titleJournal of the American Chemical Society-
dc.citation.volume144-
dc.citation.number22-
dc.citation.startPage10064-
dc.citation.endPage10074-
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.keywordPlusC-H AMIDATION-
dc.subject.keywordPlusCASCADE REACTIONS-
dc.subject.keywordPlusHYDROGEN-BONDS-
dc.subject.keywordPlusAMIDO TRANSFER-
dc.subject.keywordPlusCIS-INSERTION-
dc.subject.keywordPlusGAMMA-LACTAMS-
dc.subject.keywordPlusHYDROAMINATION-
dc.subject.keywordPlusCYCLIZATIONS-
dc.subject.keywordPlusHETEROCYCLES-
dc.subject.keywordPlusCOMPLEXES-
dc.subject.keywordAuthorCYCLIZATIONS-
dc.subject.keywordAuthorHETEROCYCLES-
dc.subject.keywordAuthorC-H AMIDATION-
dc.subject.keywordAuthorCASCADE REACTIONS-
dc.subject.keywordAuthorHYDROGEN-BONDS-
dc.subject.keywordAuthorAMIDO TRANSFER-
dc.subject.keywordAuthorCIS-INSERTION-
dc.subject.keywordAuthorGAMMA-LACTAMS-
dc.subject.keywordAuthorCOMPLEXES-
dc.subject.keywordAuthorHYDROAMINATION-
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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