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Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation

Ball, Liam T.; Corrie, Tom; Cresswell, Alex; Lloyd-Jones, Guy C.

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Authors

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LIAM BALL Liam.Ball@nottingham.ac.uk
Associate Professor

Tom Corrie

Alex Cresswell

Guy C. Lloyd-Jones



Abstract

Domino catalysis is a well-explored route to increasing the efficiency of multistep reactions. However, the kinetic features required for efficient turnover of a process where "multiple transformations are effected by a single catalytic mechanism"have not been explored in any detail. The kinetics of a nominally simple two-stage domino catalytic reaction have been analyzed by way of a gold-catalyzed coupling of two electron-deficient arylsilanes to generate an arylated fluorene. A combination of in situ interleaved 1H and 19F NMR spectroscopic kinetic measurements, kinetic simulations, and variations in substitution reveal how the catalyst partitioning between the two different cycles impacts both the rate and the selectivity of the process. The insight enables identification that sequential catalyst speciation and accumulation of the domino intermediate are general kinetic criteria for efficient domino catalysis.

Citation

Ball, L. T., Corrie, T., Cresswell, A., & Lloyd-Jones, G. C. (2020). Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation. ACS Catalysis, 10(18), 10420–10426. https://doi.org/10.1021/acscatal.0c03178

Journal Article Type Article
Acceptance Date Aug 17, 2020
Online Publication Date Aug 17, 2020
Publication Date Sep 18, 2020
Deposit Date Aug 19, 2020
Publicly Available Date Mar 28, 2024
Journal ACS Catalysis
Electronic ISSN 2155-5435
Peer Reviewed Peer Reviewed
Volume 10
Issue 18
Pages 10420–10426
DOI https://doi.org/10.1021/acscatal.0c03178
Public URL https://nottingham-repository.worktribe.com/output/4843839
Publisher URL https://pubs.acs.org/doi/10.1021/acscatal.0c03178
Additional Information This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis,copyright© American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acscatal.0c03178

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