The DOI matches its Crossref record.
Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides
Abstract
A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
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Citations
Cited by
Ynamides: Versatile Tools in Organic Synthesis
Evano, G., Coste, A., & Jouvin, K. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200905817 · Cited by 812
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
Metadata
- Authors
- Zhang, X., Zhang, Y., Huang, J., Hsung, R. P., Kurtz, K. C. M., Oppenheimer, J., Petersen, M. E., Sagamanova, I. K., Shen, L., & Tracey, M. R.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-05-01
- Volume
- 71
- Issue
- 11
- Pages
- 4170-4177
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2097840920
- Cited by
- 208
- References
- 0
- FWCI
- 6.98
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides. https://app.cochat.ai/papers/10.1021/jo060230h
- The paper
- Zhang, X., Zhang, Y., Huang, J., Hsung, R. P., Kurtz, K. C. M., Oppenheimer, J., Petersen, M. E., Sagamanova, I. K., Shen, L., & Tracey, M. R. (2006). Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides. The Journal of Organic Chemistry. https://doi.org/10.1021/jo060230h
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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.
