Utility of Hypervalent Organobismuth Compounds Binding Imido Ligand: Synthesis of Dibromotriarylbismuth Compounds and N-Ar Bond formation

Abstract

Dahlmann and Winsel has reported the synthesis of bromo(2,5-dioxo-1-pyrrolidinyl)triphenylbismuth from the reaction of triphenylbismuth and N-bromosuccinimide in acetonitrile at low temperature. However, no report exist of the reactivity of this hypervalent organobismuth compounds, due to the instability. Herein, we describe the utility of hypervalent bismuth compounds supported by imide ligands. The reaction of triarylbismuth and N-bromosuccinimide in acetoitrile in the presence of LiBr lead to dibromotriphenylbismuth in high yields. Furthermore, the Cu-catalyzed reaction of triphenylbismuth and N-bromoimides resulted in the formation of N-Ar bond.