Rowsell, Benjamin, O’Brien, Harry, Athavan, Gayathri et al. (6 more authors) (2024) The iron-catalysed Suzuki coupling of aryl chlorides. Nature Catalysis. pp. 1186-1198. ISSN 2520-1158
Abstract
The very widely exploited Suzuki biaryl coupling reaction typically requires catalysts based on palladium, but there is an increasing desire to replace this metal with a more sustainable, less expensive alternative, with catalysts based on iron being a particularly attractive target. Here we show that a simple iron-based catalyst with an N-heterocyclic carbene ligand can be used to excellent effect in the Suzuki biaryl coupling of aryl chloride substrates with aryl boronic esters activated by an organolithium reagent. Mechanistic studies suggest the possible involvement of Fe(I) as the lowest oxidation state on the catalytic manifold and show that the challenging step is not activation of the aryl chloride substrate, but rather the transmetallation step. These findings are likely to lead to a renaissance of iron-catalysed carbon–carbon bond-forming transformations with soft nucleophilic coupling partners. (Figure presented.)
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Author(s) 2024 |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number THE ROYAL SOCIETY INF\R2\202122 |
Depositing User: | Pure (York) |
Date Deposited: | 18 Oct 2024 08:40 |
Last Modified: | 19 Dec 2024 11:50 |
Published Version: | https://doi.org/10.1038/s41929-024-01234-0 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1038/s41929-024-01234-0 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:218585 |
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Description: The iron-catalysed Suzuki coupling of aryl chlorides
Licence: CC-BY 2.5