The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction
Abstract
A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of CuI and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using NaI as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents.
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Citations
Cites
Lindley, J. (1984) · Tetrahedron · doi:10.1016/s0040-4020(01)91791-0 · Cited by 2,253
Klapars, A., Antilla, J. C., Huang, X., & Buchwald, S. L. (2001) · Journal of the American Chemical Society · doi:10.1021/ja016226z · Cited by 1,021
Self-citationA General and Efficient Copper Catalyst for the Amidation of Aryl Halides
Klapars, A., Huang, X., & Buchwald, S. L. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0260465 · Cited by 851
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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
The Complementary Competitors: Palladium and Copper in C–N Cross-Coupling Reactions
Beletskaya, I. P., & Cheprakov, A. V. (2012) · Organometallics · doi:10.1021/om300683c · Cited by 454
Schaumberg, C. A., Wollgarten, M., & Rademann, K. (2015) · Physical Chemistry Chemical Physics · doi:10.1039/c5cp01153a · Cited by 22
Metadata
- Authors
- Klapars, A., & Buchwald, S. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-11-20
- Volume
- 124
- Issue
- 50
- Pages
- 14844-14845
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1994403933
- Cited by
- 437
- References
- 3
- FWCI
- 6.11
- Type
- journal article
- Language
- en
- Open access
- closed
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- Klapars, A., & Buchwald, S. L. (2002). Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction. Journal of the American Chemical Society. https://doi.org/10.1021/ja028865v
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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.
