Journal article
Exploiting carbonyl groups to control intermolecular rhodium-catalyzed alkene and alkyne hydroacylation
- Abstract:
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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 bis-phosphine 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.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Version of record, pdf, 2.7MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.7b05713
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 139
- Issue:
- 29
- Pages:
- 10142–10149
- Publication date:
- 2017-07-17
- Acceptance date:
- 2017-06-30
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Pubs id:
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pubs:702712
- UUID:
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uuid:df9ab9b4-9608-45ad-98e5-4bd051f2ed8b
- Local pid:
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pubs:702712
- Source identifiers:
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702712
- Deposit date:
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2017-07-03
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2017
- Notes:
- This is the version of record of the article. The final version is available online from American Chemical Society at: https://doi.org/10.1021/jacs.7b05713
- Licence:
- CC Attribution (CC BY)
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