The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
(NHC)Copper(I)‐Catalyzed [3+2] Cycloaddition of Azides and Mono‐ or Disubstituted Alkynes
Abstract
A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3‐triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC = N‐heterocyclic carbene). Extremely high reaction rates and excellent yields were obtained in all cases. This catalytic system fulfils the requirements of “click chemistry” with its mild and convenient conditions, notably in water or solvent free reactions and simple isolation with no purification step. Furthermore, for the first time, an internal alkyne was successfully used in this copper‐catalyzed cycloaddition reaction. DFT calculations on this particular system allowed for the proposition of a new mechanistic pathway for disubstituted alkynes.
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Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition
Rodionov, V. O., Presolski, S. I., Gardinier, S., Lim, Y.-H., & Finn, M. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja072678l · Cited by 403
More Sustainable Approaches for the Synthesis of N-Based Heterocycles
Candeias, N. R., Branco, L. C., Gois, P. M. P., Afonso, C. A. M., & Trindade, A. F. (2009) · Chemical Reviews · doi:10.1021/cr800462w · Cited by 403
Metal chelating systems synthesized using the copper(i) catalyzed azide-alkynecycloaddition
Struthers, H., Mindt, T. L., & Schibli, R. (2010) · Dalton Trans. · doi:10.1039/b912608b · Cited by 386
Metal-NHC complexes: a survey of anti-cancer properties
Teyssot, M.-L., Jarrousse, A.-S., Manin, M., Chevry, A., Roche, S., Norre, F., Beaudoin, C., Morel, L., Boyer, D., Mahiou, R., et al. (2009) · Dalton Transactions · doi:10.1039/b906308k · Cited by 384
Metadata
- Authors
- Díez‐González, S., Correa, A., Cavallo, L., & Nolan, S. P.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2006-09-28
- Volume
- 12
- Issue
- 29
- Pages
- 7558-7564
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2084944709
- Cited by
- 370
- References
- 1
- FWCI
- 16.15
- Type
- journal article
- Language
- en
- Open access
- closed
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- Díez‐González, S., Correa, A., Cavallo, L., & Nolan, S. P. (2006). (NHC)Copper(I)‐Catalyzed [3+2] Cycloaddition of Azides and Mono‐ or Disubstituted Alkynes. Chemistry – A European Journal. https://doi.org/10.1002/chem.200600961
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