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The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

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Abstract

Coupling reactions between haloarenes and arenes (including heteroarenes) that are conducted without added transition metals but in the presence of KOtBu or NaOtBu, have been a topic of great interest since their discovery in 2008. Diverse organic structures act as additives that assist these reactions. These additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions, which proceed by radical chain mechanisms. This review provides an overview of the initiation stages of these reactions.

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Acknowledgements

We thank EPSRC, GSK and the University of Strathclyde for funding (AJS).

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Authors and Affiliations

  1. Department of Pure and Applied Chemistry, University of Strathclyde, Strathclyde, Glasgow, Gl 1XL, UK

    Andrew J. Smith & John A. Murphy

  2. Flexible Discovery Unit, GlaxoSmithKline Medicines Research Centre, Stevenage, SG1 2NY, UK

    Darren L. Poole

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  1. Andrew J. Smith
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  2. Darren L. Poole
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  3. John A. Murphy
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Correspondence to John A. Murphy.

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Conflict of interest The authors declare that they have no conflict of interest.

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Smith, A.J., Poole, D.L. & Murphy, J.A. The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes. Sci. China Chem. 62, 1425–1438 (2019). https://doi.org/10.1007/s11426-019-9611-x

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