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A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
Abstract
An experimentally simple and inexpensive catalyst system was developed for the amidation of aryl halides by using 0.2-10 mol % of CuI, 5-20 mol % of a 1,2-diamine ligand, and K(3)PO(4), K(2)CO(3), or Cs(2)CO(3) as base. Catalyst systems based on N,N'-dimethylethylenediamine or trans-N,N'-dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1,2-diamine ligands could be used in the easiest cases. Aryl iodides, bromides, and in some cases even aryl chlorides can be efficiently amidated. A variety of functional groups are tolerated in the reaction, including many that are not compatible with Pd-catalyzed amidation or amination methodology.
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Citations
Cited by
Highly Efficient and Mild Copper‐Catalyzed N‐ and C‐Arylations with Aryl Bromides and Iodides
Cristau, H., Cellier, P. P., Spindler, J., & Taillefer, M. (2004) · Chemistry – A European Journal · doi:10.1002/chem.200400582 · Cited by 586
Holzer, P., Masuya, K., Furet, P., Kallen, J., Valat-Stachyra, T., Ferretti, S., Berghausen, J., Bouisset-Leonard, M., Buschmann, N., Pissot-Soldermann, C., et al. (2015) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.5b00810 · Cited by 203
Metadata
- Authors
- Klapars, A., Huang, X., & Buchwald, S. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-25
- Volume
- 124
- Issue
- 25
- Pages
- 7421-7428
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1979703254
- Cited by
- 851
- References
- 0
- FWCI
- 22.73
- Type
- journal article
- Language
- en
- Open access
- closed
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- Klapars, A., Huang, X., & Buchwald, S. L. (2002). A General and Efficient Copper Catalyst for the Amidation of Aryl Halides. Journal of the American Chemical Society. https://doi.org/10.1021/ja0260465
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