The emergence of Pd-mediated reversible oxidative addition in cross coupling, carbohalogenation and carbonylation reactions
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Date
2019-10-07
Authors
Jones, David J.
Lautens, Mark
McGlacken, Gerard P.
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Publisher
Springer Nature
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Abstract
Exploiting the reversibility of chemical processes is a long-standing tactic of organic chemists, and permeates most areas of the discipline. The notion that oxidative addition of Pd(0) to Ar–X bonds can be considered an irreversible process has been challenged, periodically, over the last 30 years. Recent examples of methodologies that harness the reversibility of oxidative addition reactions in catalytic processes have enabled access to challenging carbocyclic and heterocyclic scaffolds. This Perspective seeks to describe the development of these processes from the early proof-of-principle findings, and highlight key challenges that remain in this avenue of research. In particular, we draw attention to significant deficiencies that remain in the choice of suitable ligands and additives for these transformations. We conclude by describing how the concept of reversible oxidative addition has recently been exploited in the development of novel carbonylation reactions.
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Keywords
Cross-coupling reactions , Homogeneous catalysis , Synthetic chemistry methodology , Carbonylation , Addition reactions , Additives , Scaffolds , Statistical mechanics , Carbohalogenation , Carbonylation reactions , Catalytic process , Chemical process , Irreversible process , Oxidative addition reaction , Oxidative additions , Proof of principles
Citation
Jones, D. J., Lautens, M. and McGlacken, G. P. (2019) 'The emergence of Pd-mediated reversible oxidative addition in cross coupling, carbohalogenation and carbonylation reactions', Nature Catalysis, 2(10), pp. 843-851. doi: 10.1038/s41929-019-0361-0
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© 2019, Springer Nature Limited. This is a post-peer-review, pre-copyedit version of an article published in Nature Catalysis. The final authenticated version is available online at: http://dx.doi.org/10.1038/s41929-019-0361-0