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Issue 20, 2019
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Ni vs. Pd in Suzuki–Miyaura sp2–sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system

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Abstract

The Suzuki–Miyaura reaction is a cornerstone method for sp2–sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki–Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.

Graphical abstract: Ni vs. Pd in Suzuki–Miyaura sp2–sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system

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Article information


Submitted
08 Mar 2019
Accepted
29 Apr 2019
First published
29 Apr 2019

Org. Biomol. Chem., 2019,17, 5055-5059
Article type
Paper

Ni vs. Pd in Suzuki–Miyaura sp2–sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system

M. J. West and A. J. B. Watson, Org. Biomol. Chem., 2019, 17, 5055
DOI: 10.1039/C9OB00561G

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