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

Duen Ren Hou, Ting Chun Kuan, Yu Kai Li, Richmond Lee, Kuo Wei Huang

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

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.

Original languageEnglish
Pages (from-to)9415-9420
Number of pages6
JournalTetrahedron
Volume66
Issue number48
DOIs
StatePublished - 27 Nov 2010

Fingerprint

Dive into the research topics of 'Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides'. Together they form a unique fingerprint.

Cite this