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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
|West, Matthew J.
|Watson, Allan J. B.
|West , M J & Watson , A J B 2019 , ' Ni vs . Pd in Suzuki-Miyaura sp 2 -sp 2 cross-coupling : a head-to-head study in a comparable precatalyst/ligand system ' , Organic & Biomolecular Chemistry , vol. 17 , no. 20 , pp. 5055-5059 . https://doi.org/10.1039/C9OB00561G
|PURE UUID: e92a412d-166f-4cf9-acfc-554c6b0abebf
|We thank the University of St Andrews for a PhD studentship (MJW).
|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.
|Organic & Biomolecular Chemistry
|Copyright © 2019 The Author(s). This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C9OB00561G
|Ni vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling : a head-to-head study in a comparable precatalyst/ligand system
|University of St Andrews. School of Chemistry
|University of St Andrews. EaSTCHEM
|University of St Andrews. Sir James Mackenzie Institute for Early Diagnosis
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