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Hong, Sung You
Synthetic Organic Chemistry Laboratory
Research Interests
  • Synthetic organic chemistry, transition metals, oxidation state

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Chemo- and regioselective click reactions through nickel-catalyzed azide–alkyne cycloaddition

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dc.contributor.author Kim, Woo Gyum ko
dc.contributor.author Baek, Seung-yeol ko
dc.contributor.author Jeong, Seo Yeong ko
dc.contributor.author Nam, Dongsik ko
dc.contributor.author Jeon, Ji Hwan ko
dc.contributor.author Choe, Wonyoung ko
dc.contributor.author Baik, Mu-Hyun ko
dc.contributor.author Hong, Sung You ko
dc.date.available 2020-05-29T00:39:43Z -
dc.date.created 2020-05-21 ko
dc.date.issued 2020-05 ko
dc.identifier.citation ORGANIC & BIOMOLECULAR CHEMISTRY, v.18, no.17, pp.3374 - 3381 ko
dc.identifier.issn 1477-0520 ko
dc.identifier.uri https://scholarworks.unist.ac.kr/handle/201301/32201 -
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. ko
dc.language 영어 ko
dc.publisher ROYAL SOC CHEMISTRY ko
dc.title Chemo- and regioselective click reactions through nickel-catalyzed azide–alkyne cycloaddition ko
dc.type ARTICLE ko
dc.identifier.scopusid 2-s2.0-85084271928 ko
dc.identifier.wosid 000532260100023 ko
dc.type.rims ART ko
dc.identifier.doi 10.1039/d0ob00579g ko
dc.identifier.url https://pubs.rsc.org/en/content/articlelanding/2020/ob/d0ob00579g#!divAbstract ko
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