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Room-Temperature Aerobic C–CN Bond Activation in Nickel(II) Cyanomethyl Dicarboranyl Complex

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Organometallics 2023, 42, 15, 1997-2004
    Article

    Room-Temperature Aerobic C–CN Bond Activation in Nickel(II) Cyanomethyl Dicarboranyl Complex
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    • Mohammad Jahirul Islam
      Mohammad Jahirul Islam
      Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, South Carolina 29208, United States
      More by Mohammad Jahirul Islam
    • Kyoung Chul Park
      Kyoung Chul Park
      Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, South Carolina 29208, United States
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    • Olivia M. Manley
      Olivia M. Manley
      Department of Molecular and Structural Biochemistry, North Carolina State University, 128 Polk Hall, Raleigh, North Carolina 27695, United States
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    • Mark D. Smith
      Mark D. Smith
      Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, South Carolina 29208, United States
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    • Thomas M. Makris
      Thomas M. Makris
      Department of Molecular and Structural Biochemistry, North Carolina State University, 128 Polk Hall, Raleigh, North Carolina 27695, United States
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      Orcidhttps://orcid.org/0000-0001-7927-620X
    • Dmitry V. Peryshkov*
      Dmitry V. Peryshkov
      Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, South Carolina 29208, United States
      *Email: [email protected]
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      Orcidhttps://orcid.org/0000-0002-5653-9502
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    Organometallics

    Cite this: Organometallics 2023, 42, 15, 1997–2004
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    https://doi.org/10.1021/acs.organomet.3c00216
    Published July 12, 2023
    Copyright © 2023 American Chemical Society
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    Abstract

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    We report the synthesis and characterization of a nickel(II) complex of the dicarboranyl CNC dianionic pincer ligand, which activates acetonitrile by C–C bond cleavage. Deprotonation of the relatively acidic C–H bond of the coordinated acetonitrile with potassium t-butoxide led to the formation of the C-bound cyanomethylene ligand at the metal center. Unlike most previously characterized Ni(II) cyanoalkyls, the resulting complex exhibited quick transformation under aerobic conditions at room temperature to afford CNC-ligated nickel(II) cyanide, indicating facile cleavage of the C–CN bond. The cyanoalkyl and cyanide complexes were isolated in excellent yields and characterized by NMR spectroscopy and single-crystal X-ray diffraction. Carbon-containing products of the aerobic C–CN bond activation are hydroxyacetonitrile, formaldehyde, cyanomethyl formate, and carbon dioxide.

    Copyright © 2023 American Chemical Society

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    Supporting Information

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    CCDC 2258920–2258922 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 1 publications.

    1. Niklas F. Both, Jannik Thaens, Anke Spannenberg, Haijun Jiao, Kathrin Junge, Matthias Beller. Hydrogenation of Esters Catalyzed by Bis(N-Heterocyclic Carbene) Molybdenum Complexes. ACS Catalysis 2024, 14 (6) , 4082-4092. https://doi.org/10.1021/acscatal.4c00019
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    Organometallics

    Cite this: Organometallics 2023, 42, 15, 1997–2004
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.organomet.3c00216
    Published July 12, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

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