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A Study of the Scope and Regioselectivity of the Ruthenium-Catalyzed [3 + 2]-Cycloaddition of Azides with Internal Alkynes
Open accessAbstract
[3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of CpRuCl(PPh3)2 as catalyst in refluxing benzene have been examined, leading to 1,4,5-trisubstituted-1,2,3-triazoles. Whereas alkyl phenyl and dialkyl acetylenes undergo cycloadditions to afford mixtures of regioisomeric 1,2,3-triazoles, acyl-substituted internal alkynes react with complete regioselectivity. In addition, propargyl alcohols and propargyl amines were found to react with azides to afford single regioisomeric products.
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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
Cited by
Qin, A., Lam, J. W. Y., & Tang, B. Z. (2010) · Chemical Society Reviews · doi:10.1039/b909064a · Cited by 587
van Dijk, M., Rijkers, D. T. S., Liskamp, R. M. J., van Nostrum, C. F., & Hennink, W. E. (2009) · Bioconjugate Chemistry · doi:10.1021/bc900087a · Cited by 300
Metadata
- Authors
- Majireck, M. M., & Weinreb, S. M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-10-01
- Volume
- 71
- Issue
- 22
- Pages
- 8680-8683
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2173882888
- Cited by
- 248
- References
- 1
- FWCI
- 9.37
- Type
- journal article
- Language
- en
- Open access
- green
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- Majireck, M. M., & Weinreb, S. M. (2006). A Study of the Scope and Regioselectivity of the Ruthenium-Catalyzed [3 + 2]-Cycloaddition of Azides with Internal Alkynes. The Journal of Organic Chemistry. https://doi.org/10.1021/jo061688m
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