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Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)2: A Route to Aryl Nitriles
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    Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)2: A Route to Aryl Nitriles
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 9, 2753–2756
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    https://doi.org/10.1021/acs.orglett.8b00974
    Published April 23, 2018
    Copyright © 2018 American Chemical Society

    Abstract

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    A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C–O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b00974.

    • Experimental procedures, spectral data, and 1H, 13C NMR spectra for synthesized compounds (PDF)

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    This article is cited by 28 publications.

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    7. Yonggang Yan, Jinjin Sun, Gang Li, Liu Yang, Wei Zhang, Rui Cao, Chao Wang, Jianliang Xiao, Dong Xue. Photochemically Enabled, Ni-Catalyzed Cyanation of Aryl Halides. Organic Letters 2022, 24 (12) , 2271-2275. https://doi.org/10.1021/acs.orglett.2c00203
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    10. Andrew L. Clevenger, Ryan M. Stolley, Justis Aderibigbe, Janis Louie. Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis. Chemical Reviews 2020, 120 (13) , 6124-6196. https://doi.org/10.1021/acs.chemrev.9b00682
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    13. Yi Gan, Gaonan Wang, Xin Xie, Yuanhong Liu. Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C–O Bond Cleavage. The Journal of Organic Chemistry 2018, 83 (22) , 14036-14048. https://doi.org/10.1021/acs.joc.8b02498
    14. Fei Fan, Jinghua Tang, Meiming Luo, Xiaoming Zeng. Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)–O Bonds with a Traceless Activation Strategy. The Journal of Organic Chemistry 2018, 83 (21) , 13549-13559. https://doi.org/10.1021/acs.joc.8b02104
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    17. Ahmed H.M. Elwahy, Mohamed R. Shaaban, Ismail A. Abdelhamid. Recent advances in the synthesis of star-shaped molecules based on a 1,3,5-triazine core. 2023, 233-301. https://doi.org/10.1016/bs.aihch.2023.01.002
    18. Yi Zheng, Wenbo Liu, Xinzhe Tian, Yun-Lai Ren. Synthesis of Aryl Nitriles via Aerobic Oxidative Cleavage of Aryl C=C Bonds with (NH4)2CO3 as the Nitrogen Source. Synlett 2022, 33 (04) , 376-380. https://doi.org/10.1055/s-0041-1737761
    19. Ravindra P. Sonawane, Vikas Sikervar, Swarnendu Sasmal. 1,3,5-Triazines. 2022, 181-283. https://doi.org/10.1016/B978-0-12-818655-8.00018-4
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    22. U.S. Kanchana, Thomas V. Mathew, Gopinathan Anilkumar. Recent advances and prospects in the nickel- catalyzed cyanation. Journal of Organometallic Chemistry 2020, 920 , 121337. https://doi.org/10.1016/j.jorganchem.2020.121337
    23. Esmaeil Niknam, Farhad Panahi, Ali Khalafi‐Nezhad. Palladium‐Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source. European Journal of Organic Chemistry 2020, 2020 (18) , 2699-2707. https://doi.org/10.1002/ejoc.202000117
    24. Majid M. Heravi, Farhad Panahi, Nasser Iranpoor. Nickel-catalyzed reductive amidation of aryl-triazine ethers. Chemical Communications 2020, 56 (13) , 1992-1995. https://doi.org/10.1039/C9CC08727C
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    28. Cheng‐Tao Feng, Hong‐Juan Wei, Jing Li, Ya Peng, Kun Xu. Synthesis of Cyanide‐Functionalized Imidazo[1,5‐a]quinolines via Copper‐Mediated Aerobic Three‐Component Cyclizations. Advanced Synthesis & Catalysis 2018, 360 (24) , 4726-4730. https://doi.org/10.1002/adsc.201801060

    Organic Letters

    Cite this: Org. Lett. 2018, 20, 9, 2753–2756
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.8b00974
    Published April 23, 2018
    Copyright © 2018 American Chemical Society

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