Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources

Tyerman, Seb and Robertson, Craig M. and Murphy, John A. (2024) Radical coupling of aryl halides to arenes facilitated by Ni(COD)(DQ) and other nickel sources. Organic and Biomolecular Chemistry, 22 (5). pp. 1023-1026. ISSN 1477-0520 (https://doi.org/10.1039/D3OB01745A)

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Abstract

The air-stable complex Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone) promotes the coupling of aryl halides to arenes in the presence of KOtBu. This complex has recently been shown to perform coupling reactions based on organonickel intermediates, but in this case the coupling reactions proceed via aryl radicals as shown by our newly developed assay for aryl radicals. Coupling with this nickel source is more efficient than with Ni(COD)2, Ni(PPh3)4 and Ni(acac)2, all of which we also show to operate through aryl radical pathways.

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