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dc.contributor.authorIslam, Mohammad Shahidul
dc.contributor.authorAlammari, Abdullah Saleh
dc.contributor.authorBarakat, Assem
dc.contributor.authorAlshahrani, Saeed
dc.contributor.authorHaukka, Matti
dc.contributor.authorAl-Majid, Abdullah Mohammed
dc.date.accessioned2021-12-10T09:36:32Z
dc.date.available2021-12-10T09:36:32Z
dc.date.issued2021
dc.identifier.citationIslam, M. S., Alammari, A. S., Barakat, A., Alshahrani, S., Haukka, M., & Al-Majid, A. M. (2021). Exploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes : Synthesis and Application in Cu-Catalyzed Friedel–Crafts Asymmetric Alkylation. <i>Molecules</i>, <i>26</i>(23), Article 7408. <a href="https://doi.org/10.3390/molecules26237408" target="_blank">https://doi.org/10.3390/molecules26237408</a>
dc.identifier.otherCONVID_102339287
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/78933
dc.description.abstractFive new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The utility of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subsequently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherMDPI AG
dc.relation.ispartofseriesMolecules
dc.rightsCC BY 4.0
dc.subject.otherbis-oxazoline
dc.subject.otherbis-imidazoline
dc.subject.otherthiophene
dc.subject.otherindoles
dc.subject.otherβ-nitroolefins
dc.subject.otherasymmetric catalysis
dc.subject.otherFriedel−Crafts alkylation
dc.titleExploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes : Synthesis and Application in Cu-Catalyzed Friedel–Crafts Asymmetric Alkylation
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202112105921
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.contributor.oppiaineInorganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.relation.issn1420-3049
dc.relation.numberinseries23
dc.relation.volume26
dc.type.versionpublishedVersion
dc.rights.copyright© 2021 by the authors. Licensee MDPI, Basel, Switzerland
dc.rights.accesslevelopenAccessfi
dc.subject.ysoligandit
dc.subject.ysokompleksiyhdisteet
dc.subject.ysokemiallinen synteesi
dc.subject.ysokatalyytit
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p24741
jyx.subject.urihttp://www.yso.fi/onto/yso/p30190
jyx.subject.urihttp://www.yso.fi/onto/yso/p8468
jyx.subject.urihttp://www.yso.fi/onto/yso/p15480
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3390/molecules26237408
jyx.fundinginformationResearchers Supporting Project number (RSP-2021/64), King Saud University, Riyadh, Saudi Arabia.
dc.type.okmA1


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