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Volumn 51, Issue 3, 2010, Pages 550-553

Base and concentration effects on the product distribution in copper-promoted alkyne-azide cycloaddition: additive-free route to 5-iodo-triazoles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; BASE; COPPER DERIVATIVE; IODINE DERIVATIVE; N,N DIMETHYLANILINE; PYRIDINE; TRIAZOLE DERIVATIVE;

EID: 71649114856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.089     Document Type: Article
Times cited : (56)

References (39)
  • 1
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    • For some recent reviews see:
    • For some recent reviews see:. Meldal M., and Christian W. Chem. Rev. 108 (2008) 2952-3015
    • (2008) Chem. Rev. , vol.108 , pp. 2952-3015
    • Meldal, M.1    Christian, W.2
  • 14
    • 34250794457 scopus 로고    scopus 로고
    • Inorganic bases, under oxidative conditions, have been shown to have a profound impact by promoting the formation of 5,5′-bistriazoles:
    • Inorganic bases, under oxidative conditions, have been shown to have a profound impact by promoting the formation of 5,5′-bistriazoles:. Angell Y., and Burgess K. Angew. Chem., Int. Ed. 46 (2007) 3649-3651
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3649-3651
    • Angell, Y.1    Burgess, K.2
  • 18
    • 71649115118 scopus 로고    scopus 로고
    • note
    • 2-protons of 5-H-triazole (5.7 ppm).
  • 22
    • 67649616880 scopus 로고    scopus 로고
    • DMAP was recently shown to accelerate 1,4-triazole formation catalyzed by copper-carbene ligands, without inducing the formation of any other cyloaddition products:
    • DMAP was recently shown to accelerate 1,4-triazole formation catalyzed by copper-carbene ligands, without inducing the formation of any other cyloaddition products:. Teyssot M.-L., Chevry A., Traïnka M., El-Ghozzi M., Avignant D., and Gautier A. Chem. Eur. J. 15 (2009) 6322-6326
    • (2009) Chem. Eur. J. , vol.15 , pp. 6322-6326
    • Teyssot, M.-L.1    Chevry, A.2    Traïnka, M.3    El-Ghozzi, M.4    Avignant, D.5    Gautier, A.6
  • 28
    • 20344373411 scopus 로고    scopus 로고
    • For some examples on the synthesis of iodo-triazoles, see:
    • For some examples on the synthesis of iodo-triazoles, see:. Wu J., Deng Y.-M., and Chen Q.-Y. Synthesis (2005) 1314-1318
    • (2005) Synthesis , pp. 1314-1318
    • Wu, J.1    Deng, Y.-M.2    Chen, Q.-Y.3
  • 31
    • 71649111351 scopus 로고    scopus 로고
    • note
    • 19F NMR due to non-overlapping resonances of compounds 1 (-113.7 ppm), 2 (-112.9 ppm), and 3 (-108.9 ppm) (Table 1). However, we have also screened the effect of bases and concentrations on the CuI-promoted cycloaddition between phenylacetylene and benzyl azide, that is, non electron-effect biased substrates, and the results appeared in correlation with the trends observed in Table 1.
  • 33
    • 66049091201 scopus 로고    scopus 로고
    • It would be of interest to point out that in the absence of the azide (ratio: alkyne/DMAP/CuI-1.0/1.0/0.5), DMAP promoted a clean formation of the diynes. Although the rates of this transformation are fairly slow (20 h), as compared to some literature examples, fewer reagents as well as conditions that do not require a strong oxidant and/or strong electrophile might prove useful in certain cases. For some examples on facile alkyne homocoupling reactions see:
    • It would be of interest to point out that in the absence of the azide (ratio: alkyne/DMAP/CuI-1.0/1.0/0.5), DMAP promoted a clean formation of the diynes. Although the rates of this transformation are fairly slow (20 h), as compared to some literature examples, fewer reagents as well as conditions that do not require a strong oxidant and/or strong electrophile might prove useful in certain cases. For some examples on facile alkyne homocoupling reactions see:. Li L., Wang J., Zhang G., and Liu Q. Tetrahedron Lett. 50 (2009) 4033-4036
    • (2009) Tetrahedron Lett. , vol.50 , pp. 4033-4036
    • Li, L.1    Wang, J.2    Zhang, G.3    Liu, Q.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.