Please use this identifier to cite or link to this item: https://doi.org/10.1039/c7sc03149a
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dc.titleNickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities
dc.contributor.authorLi, W
dc.contributor.authorBoon, J.K
dc.contributor.authorZhao, Y
dc.date.accessioned2020-09-04T02:25:20Z
dc.date.available2020-09-04T02:25:20Z
dc.date.issued2018
dc.identifier.citationLi, W, Boon, J.K, Zhao, Y (2018). Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities. Chemical Science 9 (3) : 600-607. ScholarBank@NUS Repository. https://doi.org/10.1039/c7sc03149a
dc.identifier.issn2041-6520
dc.identifier.urihttps://scholarbank.nus.edu.sg/handle/10635/174365
dc.description.abstractEfficient difunctionalization of alkenes allows the rapid construction of molecular complexity from simple building blocks in organic synthesis. We present herein a nickel-catalyzed dicarbofunctionalization of alkenes using readily available organoboronic acids and organic halides in a three-component fashion. In particular, an unprecedented regioselectivity of the 1,3-dicarbofunctionalization of N-allylpyrimidin-2-amine is achieved when aryl and methyl iodides are utilized. In contrast, the use of alkyl bromides with ?-hydrogens results in 1,3-hydroarylation or oxidative 1,3-diarylation. Preliminary mechanistic studies suggest an isomerization involving nickel hydride in the 1,3-difunctionalization reactions. On the other hand, the use of alkenyl or alkynyl halides promotes alternative regioselectivities to deliver 1,2-alkenylcarbonation or intriguing 2,1-alkynylcarbonation products. Such 2,1-alkynylarylation is also applicable to N-allylbenzamide as a different class of substrates. Overall, this nickel-catalyzed process proves to be powerful in delivering versatile difunctionalized compounds using readily available reagents/catalysts and a simple procedure. © 2018 The Royal Society of Chemistry.
dc.publisherRoyal Society of Chemistry
dc.sourceUnpaywall 20200831
dc.subjectCatalysis
dc.subjectHydrocarbons
dc.subjectBuilding blockes
dc.subjectDifunctionalization
dc.subjectMechanistic studies
dc.subjectMolecular complexity
dc.subjectOrganic halides
dc.subjectOrganic synthesis
dc.subjectOrganoboronic acids
dc.subjectRapid construction
dc.subjectNickel
dc.typeArticle
dc.contributor.departmentDEPT OF CHEMISTRY
dc.description.doi10.1039/c7sc03149a
dc.description.sourcetitleChemical Science
dc.description.volume9
dc.description.issue3
dc.description.page600-607
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