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Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen
Abstract
An environmentally friendly method for synthesis of amides is presented where a simple ruthenium catalyst mediates the direct coupling between an alcohol and an amine with the liberation of two molecules of dihydrogen. The active catalyst is generated in situ from an easily available ruthenium complex, an N-heterocyclic carbene and a phosphine. The reaction allows primary alcohols to be coupled with primary alkylamines to afford the corresponding secondary amides in good yields. The amide formation presumably proceeds through a catalytic cycle where the intermediate aldehyde and hemiaminal are both coordinated to the metal catalyst.
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Citations
Cited by
Applications of Acceptorless Dehydrogenation and Related Transformations in Chemical Synthesis
Gunanathan, C., & Milstein, D. (2013) · Science · doi:10.1126/science.1229712 · Cited by 1,542
Umpolung reactivity in amide and peptide synthesis
Shen, B., Makley, D. M., & Johnston, J. N. (2010) · Nature · doi:10.1038/nature09125 · Cited by 318
Nielsen, M., Junge, H., Kammer, A., & Beller, M. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201200625 · Cited by 293
Metadata
- Authors
- Nordstrøm, L. U., Vogt, H., & Madsen, R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-12-05
- Volume
- 130
- Issue
- 52
- Pages
- 17672-17673
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2090574683
- Cited by
- 519
- References
- 0
- FWCI
- 21.21
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen. https://app.cochat.ai/papers/10.1021/ja808129p
- The paper
- Nordstrøm, L. U., Vogt, H., & Madsen, R. (2008). Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen. Journal of the American Chemical Society. https://doi.org/10.1021/ja808129p
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
