Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides |
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Authors: | Duen-Ren Hou Ting-Chun Kuan Richmond Lee Kuo-Wei Huang |
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Affiliation: | a Department of Chemistry, National Central University, 300 Jhong-Da Rd. Jhong-Li, Taoyuan 32001, Taiwan b Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore c KAUST Catalysis Center and Division of Chemical and Life Sciences and Engineering, 4700 King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia |
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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. |
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