Synthesis and application of a novel bis-1,2,3-triazole ligand containing a 2,2'-bipyrrolidine core

ARKIVOC. 2018;2018(2):280-287. doi: 10.24820/ark.5550190.p010.320. Epub 2018 Jan 28.

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.

Keywords: 1,2,3-Triazole; alkyne hydration; gold catalysis.