Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/162810
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dc.contributor.authorWang, Chang-Shengen_US
dc.contributor.authorSun, Qiaoen_US
dc.contributor.authorGarcía, Felipeen_US
dc.contributor.authorWang, Chenen_US
dc.contributor.authorYoshikai, Naohikoen_US
dc.date.accessioned2022-11-09T08:48:46Z-
dc.date.available2022-11-09T08:48:46Z-
dc.date.issued2021-
dc.identifier.citationWang, C., Sun, Q., García, F., Wang, C. & Yoshikai, N. (2021). Robust cobalt catalyst for nitrile/alkyne [2+2+2] cycloaddition: synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics*. Angewandte Chemie International Edition, 60(17), 9627-9634. https://dx.doi.org/10.1002/anie.202017220en_US
dc.identifier.issn1433-7851en_US
dc.identifier.urihttps://hdl.handle.net/10356/162810-
dc.description.abstractThe transition-metal-catalyzed [2+2+2] cycloaddition of nitriles and alkynes is an established synthetic approach to pyridines; however, these cycloadditions often rely on the use of tethered diynes or cyanoalkynes as one of the reactants. Thus, examples of efficient, fully intermolecular catalytic [2+2+2] pyridine synthesis, especially those employing unactivated nitriles and internal alkynes leading to pentasubstituted pyridines, remain scarce. Herein, we report on simple and inexpensive catalytic systems based on cobalt(II) iodide, 1,3-bis(diphenylphosphino)propane, and Zn that promote [2+2+2] cycloaddition of various nitriles and diarylacetylenes for the synthesis of a broad range of polyarylated pyridines. DFT studies support a reaction pathway involving oxidative coupling of two alkynes, insertion of the nitrile into a cobaltacyclopentadiene, and C-N reductive elimination. The resulting tetra- and pentaarylpyridines serve as precursors to hitherto unprecedented nitrogen-containing polycyclic aromatic hydrocarbons via mechanochemically assisted multifold reductive cyclodehydrogenation.en_US
dc.description.sponsorshipMinistry of Education (MOE)en_US
dc.language.isoenen_US
dc.relationMOE2016-T2-2-043en_US
dc.relationRG114/18en_US
dc.relation.ispartofAngewandte Chemie International Editionen_US
dc.rights© 2021 Wiley-VCH GmbH. All rights reserved.en_US
dc.subjectScience::Chemistryen_US
dc.titleRobust cobalt catalyst for nitrile/alkyne [2+2+2] cycloaddition: synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics*en_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doi10.1002/anie.202017220-
dc.identifier.pmid33559370-
dc.identifier.scopus2-s2.0-85102563910-
dc.identifier.issue17en_US
dc.identifier.volume60en_US
dc.identifier.spage9627en_US
dc.identifier.epage9634en_US
dc.subject.keywordsCycloadditionen_US
dc.subject.keywordsHomogeneous Catalysisen_US
dc.description.acknowledgementThis work was supported by the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2016-T2-2-043 to N.Y.) and Tier 1 (RG114/18 to N.Y.), Zhejiang Provincial Natural Science Foundation of China (Grant LY18B020007 to C.W.), and A*STAR (AME IRGA1783c0003 and A2083c0050 to F.G.). We thank Dr. Yongxin Li for his assistance with X-ray crystallographic analysis..en_US
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