Coxon, Thomas J., Fernández, Maitane, Barwick-Silk, James et al. (4 more authors) (2017) Exploiting Carbonyl Groups to Control Intermolecular Rhodium-Catalyzed Alkene and Alkyne Hydroacylation. Journal of the American Chemical Society. pp. 10142-10149. ISSN 1520-5126
Abstract
Readily available β-carbonyl-substituted aldehydes are shown to be exceptional substrates for Rh-catalyzed intermolecular alkene and alkyne hydroacylation reactions. By using cationic rhodium catalysts incorporating bisphosphine ligands, efficient and selective reactions are achieved for β-amido, β-ester, and β-keto aldehyde substrates, providing a range of synthetically useful 1,3-dicarbonyl products in excellent yields. A correspondingly broad selection of alkenes and alkynes can be employed. For alkyne substrates, the use of a catalyst incorporating the Ampaphos ligand triggers a regioselectivity switch, allowing both linear and branched isomers to be prepared with high selectivity in an efficient manner. Structural data, confirming aldehyde chelation, and a proposed mechanism are provided.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2017 American Chemical Society |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 03 Jan 2020 12:50 |
Last Modified: | 16 Oct 2024 16:17 |
Published Version: | https://doi.org/10.1021/jacs.7b05713 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1021/jacs.7b05713 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:155093 |
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Filename: jacs.7b05713.pdf
Description: Exploiting Carbonyl Groups to Control Intermolecular RhodiumCatalyzed Alkene and Alkyne Hydroacylation
Licence: CC-BY 2.5