Display options
Cite
Pušavec Kirar E, Grošelj U, Mirri G, et al. "Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions. J Org Chem. 2016;81(14):5988-97doi: 10.1021/acs.joc.6b00945.
Pušavec Kirar, E., Grošelj, U., Mirri, G., Požgan, F., Strle, G., Štefane, B., Jovanovski, V., & Svete, J. (2016). "Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions. The Journal of organic chemistry, 81(14), 5988-97. https://doi.org/10.1021/acs.joc.6b00945
Pušavec Kirar, Eva, et al. ""Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions." The Journal of organic chemistry vol. 81,14 (2016): 5988-97. doi: https://doi.org/10.1021/acs.joc.6b00945
Pušavec Kirar E, Grošelj U, Mirri G, Požgan F, Strle G, Štefane B, Jovanovski V, Svete J. "Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions. J Org Chem. 2016 Jul 15;81(14):5988-97. doi: 10.1021/acs.joc.6b00945. Epub 2016 Jul 01. PMID: 27305104.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2016 Jul 15;81(14):5988-97. doi: 10.1021/acs.joc.6b00945. Epub 2016 Jul 01.

"Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions.

The Journal of organic chemistry

Eva Pušavec Kirar, Uroš Grošelj, Giorgio Mirri, Franc Požgan, Gregor Strle, Bogdan Štefane, Vasko Jovanovski, Jurij Svete

Affiliations

  1. Faculty of Chemistry and Chemical Technology, University of Ljubljana , Ve?na Pot 113, SI-1000 Ljubljana, Slovenia.
  2. National Institute of Chemistry , Hajdrihova 19, SI-1000 Ljubljana, Slovenia.

PMID: 27305104 DOI: 10.1021/acs.joc.6b00945

Abstract

A series of 16 copper-catalyzed azomethine imine-alkyne cycloaddition (CuAIAC) reactions between four pyrazolidinone-1-azomethine imines and four terminal ynones gave the corresponding fluorescent cycloadducts as bimane analogues in very high yields. The applicability of CuAIAC was demonstrated by the fluorescent labeling of functionalized polystyrene and by using Cu-C and Cu-Fe as catalysts. Experimental evidence, kinetic measurements, and correlation between a clean catalyst surface and the reaction rate are in agreement with a homotopic catalytic system with catalytic Cu(I)-acetylide formed from Cu(0) by "in situ" oxidation. The availability of azomethine imines, mild reaction conditions, simple workup, and scalability make CuAIAC a viable supplement to the Cu-catalyzed azide-alkyne cycloaddition reaction in "click" chemistry.

Publication Types