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DC Field | Value | Language |
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dc.citation.endPage | 3381 | - |
dc.citation.number | 17 | - |
dc.citation.startPage | 3374 | - |
dc.citation.title | ORGANIC & BIOMOLECULAR CHEMISTRY | - |
dc.citation.volume | 18 | - |
dc.contributor.author | Kim, Woo Gyum | - |
dc.contributor.author | Baek, Seung-yeol | - |
dc.contributor.author | Jeong, Seo Yeong | - |
dc.contributor.author | Nam, Dongsik | - |
dc.contributor.author | Jeon, Ji Hwan | - |
dc.contributor.author | Choe, Wonyoung | - |
dc.contributor.author | Baik, Mu-Hyun | - |
dc.contributor.author | Hong, Sung You | - |
dc.date.accessioned | 2023-12-21T17:38:42Z | - |
dc.date.available | 2023-12-21T17:38:42Z | - |
dc.date.created | 2020-05-21 | - |
dc.date.issued | 2020-05 | - |
dc.description.abstract | Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity. | - |
dc.identifier.bibliographicCitation | ORGANIC & BIOMOLECULAR CHEMISTRY, v.18, no.17, pp.3374 - 3381 | - |
dc.identifier.doi | 10.1039/d0ob00579g | - |
dc.identifier.issn | 1477-0520 | - |
dc.identifier.scopusid | 2-s2.0-85084271928 | - |
dc.identifier.uri | https://scholarworks.unist.ac.kr/handle/201301/32201 | - |
dc.identifier.url | https://pubs.rsc.org/en/content/articlelanding/2020/ob/d0ob00579g#!divAbstract | - |
dc.identifier.wosid | 000532260100023 | - |
dc.language | 영어 | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.title | Chemo- and regioselective click reactions through nickel-catalyzed azide–alkyne cycloaddition | - |
dc.type | Article | - |
dc.description.isOpenAccess | FALSE | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.type.docType | Article | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordPlus | CUAAC REACTIONS | - |
dc.subject.keywordPlus | MILD | - |
dc.subject.keywordPlus | REACTIVITY | - |
dc.subject.keywordPlus | CHEMOSELECTIVITY | - |
dc.subject.keywordPlus | 1,2,3-TRIAZOLES | - |
dc.subject.keywordPlus | CONSTRUCTION | - |
dc.subject.keywordPlus | PERFORMANCE | - |
dc.subject.keywordPlus | LIGATION | - |
dc.subject.keywordPlus | ORIGIN | - |
dc.subject.keywordPlus | SCOPE | - |
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