The DOI matches its Crossref record; 20 of the 20 references it cites were found in a registry or an index.
Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition
Abstract
Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand arms were evaluated by absolute rate measurements under relatively dilute conditions by aliquot quenching kinetics and by relative rate measurements under concentrated conditions by reaction calorimetry. Benzimidazole-based ligands with pendant alkylcarboxylate arms proved to be advantageous in the latter case. The catalyst system was shown to involve more than one active species, providing a complex response to changes in pH and buffer salts and the persistence of high catalytic rate in the presence of high concentrations of coordinating ligands. The water-soluble ligand (BimC4A)3 was found to be especially convenient for the rapid and high-yielding synthesis of several functionalized triazoles with 0.01-0.5 mol % Cu.
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
1,3-Dipolar Cycloaddition Chemistry
Padwa, A. (1984) · Medical Entomology and Zoology · Cited by 3,241
Profiling Enzyme Activities In Vivo Using Click Chemistry Methods
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Mechanism of the Ligand‐Free CuI‐Catalyzed Azide–Alkyne Cycloaddition Reaction
Rodionov, V. O., Fokin, V. V., & Finn, M. G. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200461496 · Cited by 625
Self-citationPEG- and Peptide-Grafted Aliphatic Polyesters by Click Chemistry
Parrish, B., Breitenkamp, R. B., & Emrick, T. (2005) · Journal of the American Chemical Society · doi:10.1021/ja050310n · Cited by 579
Synthesis of Sugar Arrays in Microtiter Plate
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“Clicking” Functionality onto Electrode Surfaces
Collman, J. P., Devaraj, N. K., & Chidsey, C. E. D. (2004) · Langmuir · doi:10.1021/la0362977 · Cited by 479
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(NHC)Copper(I)‐Catalyzed [3+2] Cycloaddition of Azides and Mono‐ or Disubstituted Alkynes
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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
Bioorthogonal Chemistry and Its Applications
Bird, R. E., Lemmel, S. A., Yu, X., & Zhou, Q. A. (2021) · Bioconjugate Chemistry · doi:10.1021/acs.bioconjchem.1c00461 · Cited by 409
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
Johnson, J. A., Finn, M. G., Koberstein, J. T., & Turro, N. J. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800208 · Cited by 320
Self-citation
Metadata
- Authors
- Rodionov, V. O., Presolski, S. I., Gardinier, S., Lim, Y.-H., & Finn, M. G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-10-01
- Volume
- 129
- Issue
- 42
- Pages
- 12696-12704
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2036045099
- Cited by
- 403
- References
- 20
- FWCI
- 12.51
- Type
- journal article
- Language
- en
- Open access
- closed
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- Rodionov, V. O., Presolski, S. I., Gardinier, S., Lim, Y.-H., & Finn, M. G. (2007). Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition. Journal of the American Chemical Society. https://doi.org/10.1021/ja072678l
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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