Tris-(benzyltriazolylmethyl)amine
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tris-(benzyltriazolylmethyl)amine (TBTA) is a tertiary amine containing the 1,2,3-triazole moiety. When used as a ligand, complexed to copper(I), it allows for quantitative, regioselective Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic solvents.
It is believed that the ligand promotes catalysis through the stabilization of the copper(I)-oxidation state, while still allowing for the catalytic cycle of the CuAAC reaction to proceed. Tim's ligand is named after Tim Chan, who developed this molecule for use as a biological labelling tool while working as a graduate student for K. Barry Sharpless. In technical literature this catalyst is referred to as TBTA.
X-ray analysis of the Cu(I) complex of tris(benzyltriazolylmethyl)amine revealed an unusual dinuclear dication with one triazole unit bridging two metal centers, and is an effective catalyst for the 'click' cycloaddition reaction. The X-ray structure of the complex of TBTA with Cu(II) is trigonal bipyramidal and can be reduced to an active 'click' catalyst by sodium ascorbate.
[edit] References
- Timothy R. Chan, Robert Hilgraf, K. Barry Sharpless, and Valery V. Fokin (2004). "Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis". Org. Lett. 6 (17): 2853–2855. doi:.
- Donnelly, P.S., Zanatta, S.D., Zammit, S.C., White, J.M., Williams, S.J. (2008). "‘“Click” Cycloaddition Catalysts: Copper(I) and Copper(II) tris-(Triazolylmethyl)amine Complexes’". Chem. Commun.: 2459–2461. doi:.
