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Issue 5, 2019
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Base induced C–CN bond cleavage at room temperature: a convenient method for the activation of acetonitrile

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Abstract

An efficient and simple method was explored for the C–CN cleavage of acetonitrile in air at room temperature. The activation reaction was mediated by the mononuclear complex of [MII(PyN2Ph2Me2)(OH)]1− (M = Cu, Ni; PyN2Ph2Me2 = N,N′-bis(2,6-dimethylphenyl)-2,6-pyridinedicarboxamidate(2-)) in the presence of NaOH. Acetonitrile splits into cyanide and formaldehyde via the intermediate η2-enaminemethide isomer species of [MII–(CH[double bond, length as m-dash]C[double bond, length as m-dash]NH)] and [MII–(N[double bond, length as m-dash]C[double bond, length as m-dash]CH2)]. A base-dioxygen induced reaction mechanism was proposed based on the crystal structures of intermediate complexes and organic adducts, which were characterized by X-ray crystallography, EPR spectroscopy, GC-MS techniques and DFT calculations. The nitrile-activated product [CuII–CN] was utilized as a cyanide source for the catalytic cyanation of iodobenzene, phenylboronic acid and 2-phenylpyridine.

Graphical abstract: Base induced C–CN bond cleavage at room temperature: a convenient method for the activation of acetonitrile

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Publication details

The article was received on 21 Nov 2018, accepted on 21 Feb 2019 and first published on 22 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QI01258J
Inorg. Chem. Front., 2019,6, 1135-1140

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    Base induced C–CN bond cleavage at room temperature: a convenient method for the activation of acetonitrile

    X. Zhang, Z. Zhang, S. Xiang, Y. Zhu, C. Chen and D. Huang, Inorg. Chem. Front., 2019, 6, 1135
    DOI: 10.1039/C8QI01258J

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