Synthesis of an Indazole/Indazolium Phosphine Ligand Scaffold and Its Application in Gold(I) Catalysis

Advances in ligand development have allowed for the fine-tuning of gold catalysis. To contribute to this field, we designed an indazole phosphine ligand scaffold that allows facile introduction of cationic charge through methylation. With minimal changes to the structure upon methylation, we could assess the importance of the electronic effects of the insertion of a positive charge on the catalytic activity of the resulting gold(I) complex. Using the benchmark reactions of propargyl amide cyclization and enyne cyclization with and without hexafluoroisopropanol (HFIP), we observed marked differences in the catalytic activities of the neutral and cationic gold species.

Automated summary

This study presents the design of a novel ligand structure, allowing facile introduction of cationic charge through methylation, to investigate the effect of positive charge insertion on the catalytic activity of gold catalysts. Experimental results demonstrate significant differences in catalytic activity between neutral and cationic gold species.