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Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition
Abstract
Cu(II) salts accelerate azide-alkyne cycloaddition reactions in alcoholic solvents without reductants such as sodium ascorbate. Spectroscopic observations suggest that Cu(II) undergoes reduction to catalytic Cu(I) species via either alcohol oxidation or alkyne homocoupling, or both, during an induction period. The reactions involving 2-picolylazide are likely facilitated by its chelation to Cu(II). The highly exothermic reaction between 2-picolylazide and propargyl alcohol completes within 1-2 min in the presence of as low as 1 mol % Cu(OAc)(2).
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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
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McKay, C. S., & Finn, M. G. (2014) · Chemistry & Biology · doi:10.1016/j.chembiol.2014.09.002 · Cited by 768
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Metadata
- Authors
- Brotherton, W. S., Michaels, H. A., Simmons, J. T., Clark, R. J., Dalal, N. S., & Zhu, L.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-10-07
- Volume
- 11
- Issue
- 21
- Pages
- 4954-4957
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2063464067
- Cited by
- 223
- References
- 1
- FWCI
- 8.62
- Type
- journal article
- Language
- en
- Open access
- closed
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- Brotherton, W. S., Michaels, H. A., Simmons, J. T., Clark, R. J., Dalal, N. S., & Zhu, L. (2009). Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition. Organic Letters. https://doi.org/10.1021/ol9021113
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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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