Nickel versus palladium in cross-coupling catalysis : on the role of substrate coordination to zerovalent metal complexes

Cooper, Alasdair K. and Burton, Paul M. and Nelson, David J. (2019) Nickel versus palladium in cross-coupling catalysis : on the role of substrate coordination to zerovalent metal complexes. Synthesis. ISSN 0039-7881

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    Abstract

    We report a detailed comparison of the effect of coordinating functional groups on the performance of Suzuki-Miyaura reactions catalysed by nickel and palladium, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has a range of effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.