1,2,3-Triazoles as Crucial Ligands in Metal Catalysis

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The understanding of basic ligand-metal interactions translates to the development of new catalysts to promote important and challenging chemical transformations using relatively simple precursors. Although the 1,2,3-triazole ring system was introduced to the chemical community via "click-chemistry," with numerous applications applied to chemical, biological and materials research, most of the reported efforts focused on the application of this efficient linking strategy to bring functional groups in close proximity. In contrast, little is known about the fundamental reactivity of TAs upon interaction with catalytic metals. This grant will develop an extensive set of catalysts based upon such interaction. This project is also integrated into an outreach program to introduce undergraduate students from the state of West Virginia to advanced organic synthesis and catalysis.Through this award, funded by the Chemical Synthesis Program (SYN) of the Division of Chemistry, Prof. X. Shi from the West Virginia University investigates the coordination ability of 1,2,3-triazoles (TAs) toward transition metal cations. With the ability to prepare various TA-derivatives, Prof. Shi's lab has studied TA-coordination with various transition metal cations over the last five years, with novel TA complexes obtained with excellent stability and striking reactivity. These discoveries have challenged the assumption that TAs are poor ligands. In this project, new TA-complexes are being synthesized and investigated, both for fundamental reasons and for industrial applications (new catalyst design). These systems include triazole-Au-catalyzed alkyne activation and triazole-directed C-H activation.