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Synthesis 2020; 52(04): 565-573
DOI: 10.1055/s-0039-1690045
paper
© Georg Thieme Verlag Stuttgart · New York

Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes

Alasdair K. Cooper
a   WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland   eMail: david.nelson@strath.ac.uk
,
Paul M. Burton
b   Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK
,
David J. Nelson∗
a   WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland   eMail: david.nelson@strath.ac.uk
› InstitutsangabenWe thank Syngenta and the Engineering and Physical Sciences Research Council for an Industrial CASE Studentship for AKC (EP/P51066X/1), and the University of Strathclyde for a Chancellor’s Fellowship for DJN (2014–18). We are grateful to the Carnegie Trust for the Universities of Scotland for a Research Incentive Grant (RIG008165).
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Publikationsverlauf

Received: 17. November 2019

Accepted after revision: 16. Dezember 2019

Publikationsdatum:
19. Dezember 2019 (online)

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Dedicated to Gavin Bain on the occasion of his retirement, in acknowledgement of his many years of service within the Department of Pure and Applied Chemistry at the University of Strathclyde.

Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

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.

Key words

nickel catalysis - cross-coupling - robustness screening - reaction­ mechanisms - structure–activity relationships

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690045. All data underpinning this publication are openly available from the University of Strathclyde KnowledgeBase at https://doi.org/10.15129/48cb8d5c-ea93-474a-9c7b-7f847cfdfe89.
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