Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 4, Pages 565-573Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690045
Keywords
nickel catalysis; cross-coupling; robustness screening; reaction mechanisms; structure-activity relationships
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Funding
- Syngenta [EP/P51066X/1]
- Engineering and Physical Sciences Research Council [EP/P51066X/1]
- University of Strathclyde [2014-18]
- Carnegie Trust for the Universities of Scotland [RIG008165]
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A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki-Miyaura reactions catalysed by nickel and palladium is reported, 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 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.
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