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

Matthew J. West, Allan J. B. Watson

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9 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)5055-5059
JournalOrganic & Biomolecular Chemistry
Volume17
Issue number20
Early online date29 Apr 2019
DOIs
Publication statusPublished - 28 May 2019

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