Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/162810
Title: Robust cobalt catalyst for nitrile/alkyne [2+2+2] cycloaddition: synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics*
Authors: Wang, Chang-Sheng
Sun, Qiao
García, Felipe
Wang, Chen
Yoshikai, Naohiko
Keywords: Science::Chemistry
Issue Date: 2021
Source: 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
Project: MOE2016-T2-2-043
RG114/18 
Journal: Angewandte Chemie International Edition 
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.
URI: https://hdl.handle.net/10356/162810
ISSN: 1433-7851
DOI: 10.1002/anie.202017220
Rights: © 2021 Wiley-VCH GmbH. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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