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Issue 24, 2018
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A mild electroassisted synthesis of (hetero)arylphosphonates

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The electrochemically-assisted synthesis of (hetero)arylphosphonates from (hetero)aryl halides and dimethyl phosphite is described. Very mild and simple conditions are employed as the cross-coupling is carried out in galvanostatic mode, in an undivided cell at room temperature, using NiBr2bpy as the easily available pre-catalyst and acetonitrile as the solvent. In addition, both aryl bromides and iodides can be used as well, providing the corresponding (hetero)arylphosphonates in generally good yields. A mechanism involving the in situ generation of a Ni ate complex is proposed.

Graphical abstract: A mild electroassisted synthesis of (hetero)arylphosphonates

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The article was received on 27 Feb 2018, accepted on 30 May 2018 and first published on 01 Jun 2018

Article type: Paper
DOI: 10.1039/C8OB00500A
Citation: Org. Biomol. Chem., 2018,16, 4495-4500
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    A mild electroassisted synthesis of (hetero)arylphosphonates

    S. Sengmany, A. Ollivier, E. Le Gall and E. Léonel, Org. Biomol. Chem., 2018, 16, 4495
    DOI: 10.1039/C8OB00500A

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