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DC Field | Value | Language |
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dc.contributor.author | Wang, Chang-Sheng | en_US |
dc.contributor.author | Sun, Qiao | en_US |
dc.contributor.author | García, Felipe | en_US |
dc.contributor.author | Wang, Chen | en_US |
dc.contributor.author | Yoshikai, Naohiko | en_US |
dc.date.accessioned | 2022-11-09T08:48:46Z | - |
dc.date.available | 2022-11-09T08:48:46Z | - |
dc.date.issued | 2021 | - |
dc.identifier.citation | Wang, 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.202017220 | en_US |
dc.identifier.issn | 1433-7851 | en_US |
dc.identifier.uri | https://hdl.handle.net/10356/162810 | - |
dc.description.abstract | The 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.sponsorship | Ministry of Education (MOE) | en_US |
dc.language.iso | en | en_US |
dc.relation | MOE2016-T2-2-043 | en_US |
dc.relation | RG114/18 | en_US |
dc.relation.ispartof | Angewandte Chemie International Edition | en_US |
dc.rights | © 2021 Wiley-VCH GmbH. All rights reserved. | en_US |
dc.subject | Science::Chemistry | en_US |
dc.title | Robust cobalt catalyst for nitrile/alkyne [2+2+2] cycloaddition: synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics* | en_US |
dc.type | Journal Article | en |
dc.contributor.school | School of Physical and Mathematical Sciences | en_US |
dc.identifier.doi | 10.1002/anie.202017220 | - |
dc.identifier.pmid | 33559370 | - |
dc.identifier.scopus | 2-s2.0-85102563910 | - |
dc.identifier.issue | 17 | en_US |
dc.identifier.volume | 60 | en_US |
dc.identifier.spage | 9627 | en_US |
dc.identifier.epage | 9634 | en_US |
dc.subject.keywords | Cycloaddition | en_US |
dc.subject.keywords | Homogeneous Catalysis | en_US |
dc.description.acknowledgement | This 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 |
item.fulltext | No Fulltext | - |
item.grantfulltext | none | - |
Appears in Collections: | SPMS Journal Articles |
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