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Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides

Journal Article


Abstract


  • A combined experimental and theoretical study of ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) reactions is presented and various electronic analyses were conducted to provide a basis in understanding the observed regioselectivity of the 1,2,3-triazole products. Computational studies using density functional theory (DFT) and atoms in molecules quantum theory (AIM) further yield fresh details on the electronic factors that determine the regioselectivity in the RuAAC. It is found that the formation of 1,2,3-triazole products is irreversible and from the Hammett study, the pathway involving a vinyl cationic intermediate is ruled out. The electronic effect favors the formation of 5-electron-donating-group substituted-1,2,3-trizoles. © 2010 Elsevier Ltd. All rights reserved.

Publication Date


  • 2010

Citation


  • Hou, D. R., Kuan, T. C., Li, Y. K., Lee, R., & Huang, K. W. (2010). Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides. Tetrahedron, 66(48), 9415-9420. doi:10.1016/j.tet.2010.09.099

Scopus Eid


  • 2-s2.0-78049462274

Start Page


  • 9415

End Page


  • 9420

Volume


  • 66

Issue


  • 48

Abstract


  • A combined experimental and theoretical study of ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) reactions is presented and various electronic analyses were conducted to provide a basis in understanding the observed regioselectivity of the 1,2,3-triazole products. Computational studies using density functional theory (DFT) and atoms in molecules quantum theory (AIM) further yield fresh details on the electronic factors that determine the regioselectivity in the RuAAC. It is found that the formation of 1,2,3-triazole products is irreversible and from the Hammett study, the pathway involving a vinyl cationic intermediate is ruled out. The electronic effect favors the formation of 5-electron-donating-group substituted-1,2,3-trizoles. © 2010 Elsevier Ltd. All rights reserved.

Publication Date


  • 2010

Citation


  • Hou, D. R., Kuan, T. C., Li, Y. K., Lee, R., & Huang, K. W. (2010). Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides. Tetrahedron, 66(48), 9415-9420. doi:10.1016/j.tet.2010.09.099

Scopus Eid


  • 2-s2.0-78049462274

Start Page


  • 9415

End Page


  • 9420

Volume


  • 66

Issue


  • 48