Abstract
Herein, we describe the synthesis of a novel bis-1,2,3-triazole ligand which contains an internal N-alkylated 2,2'-bipyrrolidine linker. By using simple starting materials, the ligand could be generated in good yield through several synthetic steps. To investigate the potential for the application of this ligand in transition metal catalysis, we generated a bis-Au(I) complex in nearly quantitative yield and examined its reactivity in the context of alkyne hydration. Both alkyl and aryl terminal alkynes could be efficiently converted to their corresponding ketones in nearly quantitative yields with only 1% catalyst loading under mild conditions.
Highlights
Ligand design has been integral to the realization of new catalytic approaches relying on transition metals
We have demonstrated that these electron-poor heterocycles have a high affinity to bind to mid to late transition metals such as Rh,[1] Pd,2 Fe,[3] Ir,4 and Au.[5,6,7,8,9]
Based on NMR data, the ligand is interacting with Au(I) in a very dynamic fashion. This catalyst exhibits good thermal stability and high efficiency in the hydration reaction of terminal aryl and alkyl alkynes, which proves that the tertiary amines within the ligand do not lead to Au(I) deactivation
Summary
Ligand design has been integral to the realization of new catalytic approaches relying on transition metals. With the desired compound in hand, we generated the bis-Au complex 8 by treating the ligand with two equivalents of Ph3PAuCl and two equivalents of AgOTf. Upon the addition of AgOTf, a white precipitate (AgCl) could be seen almost immediately. It is important to note that the broad nature of the NMR spectra for the complex suggests some dynamic bonding behavior in solution.
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