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

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Title
Chemo- and regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition
Author(s)
Woo Gyum Kim; Seung-yeol Baek; Seo Yeong Jeong; Dongsik Nam; Ji Hwan Jeon; Wonyoung Choe; Mu-Hyun Baik; Sung You Hong
Subject
CUAAC REACTIONS, ; MILD, ; REACTIVITY, ; CHEMOSELECTIVITY, ; 1,2,3-TRIAZOLES, ; CONSTRUCTION, ; PERFORMANCE, ; LIGATION, ; ORIGIN, ; SCOPE
Publication Date
2020-05
Journal
ORGANIC & BIOMOLECULAR CHEMISTRY, v.18, no.17, pp.3374 - 3381
Publisher
ROYAL SOC CHEMISTRY
Abstract
© The Royal Society of Chemistry 2020 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
URI
https://pr.ibs.re.kr/handle/8788114/8620
DOI
10.1039/d0ob00579g
ISSN
1477-0520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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