Mechanistic considerations for transmetalation at nickel(II) and palladium(II) complexes: towards improved catalysis

Nicholas S. D. Solomon; Sinead T. Keaveney

doi:10.1071/CH25103

REVIEW (Open Access)

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Mechanistic considerations for transmetalation at nickel(II) and palladium(II) complexes: towards improved catalysis

Nicholas S. D. Solomon

^A ^* and Sinead T. Keaveney

^B ^*

+ Author Affiliations

- Author Affiliations

^A School of Natural Sciences, Macquarie University, Sydney, NSW 2109, Australia.

^B School of Science, and Molecular Horizons Institute, University of Wollongong, Wollongong, NSW 2522, Australia.

Dr Nicholas Solomon received his PhD in 2025 from Macquarie University in Sydney, Australia, having studied organometallic reaction mechanisms under the supervision of Dr Sinead Keaveney. Following this, he joined the Dementia Research Centre at Macquarie University as a post-doctoral researcher in the group of Ole Tietz. His work now focuses on developing small molecule and peptide-based therapeutics, as well as synthetic strategies towards these applications.

Dr Sinead Keaveney received her PhD in 2016 from UNSW Australia, in the field of physical organic chemistry under the supervision of Assoc. Prof. Jason Harper. Following a post-doctoral position at RWTH Aachen University, Germany, with Prof. Franziska Schoenebeck, and a research fellowship at Macquarie University, Australia, she joined the University of Wollongong in 2021 as a lecturer. Her research program is focused on developing new synthetic methodology through combined experimental, computational and mechanistic studies.

^* Correspondence to: nicholas.solomon@mq.edu.au, sineadk@uow.edu.au

Handling Editor: Curt Wentrup

Australian Journal of Chemistry 78, CH25103 https://doi.org/10.1071/CH25103

Submitted: 4 July 2025 Accepted: 1 September 2025 Published online: 30 September 2025

© 2025 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

Palladium and nickel catalysed cross-coupling reactions are used extensively in organic synthesis, with state-of-the-art cross-coupling methodology enabling access to diverse building blocks in an efficient and selective manner. In recent years, there has been growing interest in using nickel-based catalysts for cross-coupling reactions, in place of the more commonly used palladium catalysts. This is motivated by both the unique reactivity that can be accessed when using nickel catalysts, and due to nickel being cheaper and more earth abundant than palladium. Despite these advantages, larger catalyst quantities and higher reaction temperatures are often required when using nickel, increasing cost and environmental impact. As such, in order to design more efficient nickel-catalysed cross-coupling reactions, a greater understanding of how these catalysts operate is required. In this review, mechanistic studies on the key transmetalation step of typical palladium and nickel-catalysed cross-couplings are discussed, with a focus on how catalyst structure affects the efficiency of transmetalation at palladium(II) and nickel(II).

Keywords: cross coupling, density functional theory, DFT, kinetics, mechanism, nickel catalysis, palladium catalysis, transition state, transmetalation.

Biographies

Dr Nicholas Solomon received his PhD in 2025 from Macquarie University in Sydney, Australia, having studied organometallic reaction mechanisms under the supervision of Dr Sinead Keaveney. Following this, he joined the Dementia Research Centre at Macquarie University as a post-doctoral researcher in the group of Ole Tietz. His work now focuses on developing small molecule and peptide-based therapeutics, as well as synthetic strategies towards these applications.

Dr Sinead Keaveney received her PhD in 2016 from UNSW Australia, in the field of physical organic chemistry under the supervision of Assoc. Prof. Jason Harper. Following a post-doctoral position at RWTH Aachen University, Germany, with Prof. Franziska Schoenebeck, and a research fellowship at Macquarie University, Australia, she joined the University of Wollongong in 2021 as a lecturer. Her research program is focused on developing new synthetic methodology through combined experimental, computational and mechanistic studies.

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